Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Article abstract of DOI:10.1039/c7gc03534a

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)₂/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.

Full text of DOI:10.1039/c7gc03534a

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Ni‐Catalyzed Chemoselective Alcoholysis of N‐Acyloxazolidinones
Pei‐Qiang Huanga,b* and Hui Genga
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Although N‐acyloxazolidinone‐based (catalytic) asymmetric stoichiometric to catalytic.9 Later on, many catalytic
synthetic methodologies occupies an important position in modern enantioselective addition reactions of achiral N‐
organic synthesis, the catalytic cleavage of the (chiral)auxiliary acyloxazolidinones 1B have been developed (Scheme 1b).10 In
remains underdeveloped. We report the Ni(cod)2/bipyr.‐catalyzed contrast to the significant progresses made on the catalytic
alcoholysis of N‐acyloxazolidinones to deliver esters. The reaction reactions
is broad in scope for both N‐acyloxazolidinone substrates and transformations of the resulting N‐acyloxazolidinone
alcohol nucleophiles, and displayed good functional group derivatives (2A 2B) by cleaving the (chiral) auxiliary rely largely
tolerance and excellent chemoselectivity.
gram‐scale on the use of stoichiometric amount of promotors11‐13 (Scheme
of
N‐acyloxazolidinones,
the
subsequent
/
A
methanolysis allowed the enantioselective synthesis of the C22‐ 1c), catalytic version (Scheme 1d) remains underdeveloped. In
C26 segment of a close analogue of the potent immunosuppressant this regard, Shi’s rhodium/copper‐catalyzed annulation of N‐
agent FK506.
aroyloxazolidinones with alkynes14 leading to indenones is a
rare example. One of the most demanding transformations of
25 years ago the concept of Green Chemistry was put forward.1
In 1991, Trost advanced the concept of atom‐economy and
indicated that transition metal‐catalyzed selective and
economical methods represent an important starting point for
the long‐term goal of atom economy.2 Today, catalysis is well‐
recognized as a key strategy for green chemistry.3 Although
tremendous progresses have been made over the past 25 years,
and since the 21st century catalytic reactions have been
honored three times by the Nobel Prizes for Chemistry,4,5
current organic synthesis still largely relies on stoichiometric
transformations as can be seen from the majority of steps of the
reported total syntheses of natural products.6
N‐acyloxazolidinone derivatives (2A/ 2B) is undoubtedly the
alcoholysis. The requirements for a synthetically useful
alcoholysis reaction reside in good selectivity for the exocyclic
Since the seminal work of Evans started from early 1980s,7
chiral‐non‐racemic N‐acyloxazolidinones 1A have become a
versatile platform for several important asymmetric
transformations including α–functionalization of the carbonyl
group, aldol addition, Michael addition, Diels‐Alder reaction, etc
(Scheme 1a).8 Many of those reactions have been evolved from
a. Department of Chemistry, Fujian Provincial Key Laboratory of Chemical Biology,
iChEM (Collaborative Innovation Center of Chemistry for Energy Materials),
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen,
Fujian 361005, P. R. China. E‐mail: pqhuang@xmu.edu.cn; Tel: +86‐592‐2182240
b. State Key Laboratory of Elemento‐Organic Chemistry, Nankai University, Tianjin
300071, P. R. China.
Scheme 1 Generic scheme for the diastereo- and enantio-selective reactions of
N-acyloxazolidinones and subsequent transformations.
† Electronic Supplementary Information (ESI) available: screened conditions,
experimental procedures, compounds characterization data, 1H and 13C NMR
spectra of prepared compounds, HPLC diagrams. See DOI: 10.1039/x0xx00000x
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cleavage,11 versatility for different product classes yielded from entries 1‐7). To our delight, Ni(cod)2/PCy3‐catalyzed reaction
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DOI: 10.1039/C7GC03534A
different asymmetric reactions, versatility for different alcohol afforded the desired ester 3a in 27% yield. Thus, Ni(cod)2 was
nucleophiles, good functional group tolerance, and mild selected as a catalyst for the methanolysis of 1a, and its
conditions to avoid racemization at stereogenic center.
combination with different ligands were examined. While low
Although several protocols for the alcoholysis of N‐
acyloxazolidinone derivatives (2A/ 2B) using an excess or
Table 1 Catalyst and ligand screening for the methanolysis of N‐acyloxazolidinone 1aa
stoichiometric quantities of base,11 acid12 or Ti(OR)413 have been
developed, very few examples of the chemoselective catalytic
alcoholysis of N‐acyloxazolidinones have been reported. In the
course of the enantioselective total synthesis of altohyrtin C
(spongistatin 2), Evans, and Sibi used rare‐earth metal triflate
Sm(OTf)3 as an efficient catalyst for the methanolysis or
aminolysis of an alkylated N‐acyloxazolidinone.15
Subsequently, other Lewis acid‐catalyzed alcoholysis methods
have been reported by the groups of Fukuzawa (LaI3),16 Otera
{[t‐Bu2SnCl(OH)]2, MgBr2 and Sc(OTf)3},17 and Collin (SmI2),18
respectively. Although some of those methods have found
synthetic applications, they suffered from at least one drawback
such as the need to use a large excess of alcohol nucleophile
(e.g. as a solvent) or stoichiometric amount of Lewis acid,16
limited scope for substrates (e.g. inapplicable to aldol adducts)
or for alcohols (e.g. inapplicable to benzyl alcohol). Crimmins
reported that N‐acyloxazolidinethione auxiliaries are more
easily cleaved.19 Wu and co‐workers has developed the DMAP‐
catalyzed removal of thiazolidinethione auxiliaries with benzyl
alcohol.20 In 2012, Saito reported a conceptually new method
Cat. (10
mol%)
Yield (%)b
Entry
Ligand (10 mol%)
3a
27
17
34
24
34
94
87
86
95
54
1a
65
1
2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
NiCp2
PCy3
PPh3
PnBu3
77
3
56
4
Box1
75
5
Box2
62
6
SIPr
trace
10
7
IPr
8
SIMes
10
9
IMes
trace
38
10
11
12
13 d
14 d
15 d
16 d
1,10‐phenanthroline
2,2'‐bipyr.
2,2'‐bipyr.
2,2'‐bipyr.
2,2'‐bipyr.
2,2'‐bipyr.
2,2'‐bipyr.
95 (91)c
trace
trace
trace
trace
trace
trace
88
consisting of double molecular recognition of
‐dicarbonyl
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
96 (92)c
95 (93)c,e
94 f
derivatives with aminoorganoboron (AOB) complexes followed
by in situ methanolysis.21 Using this method, catalytic
alcoholysis of N‐acyloxazolidinones has been achieved
regioselectively. However, since only a smaller alcohol can be
recognized, the method is restricted to alcoholysis with MeOH.
In addition, AOB complexes are not commercially available.
To the best of our knowledge, up to date, transition metal‐
catalyzed alcoholysis of N‐acyloxazolidinones has hitherto been
unknown.
97 (92)c,g
In the field of organic catalytic transformation, due to the
decline of natural resource of precious metals such as palladium
and the associated price increases, the development of catalytic
reactions based on inexpensive earth abundant first‐row
transition metals has attracted much attention.22,23 In this
context, the use of nickel in catalysis has emerged as a new
frontier.23 This is due, on one hand, to its cheapness (nickel costs
about 0.05% of price of palladium and 0.01% of price of
platinum), and on the other hand, to its multiple advantageous
characteristics as compare with palladium.23
In connection with our interest in developing synthetic
methodologies for the direct transformation of amides,24 we
disclosed very recently the first Ni/bis‐NHC‐catalyzed cross‐
coupling of N‐acylpyrrole‐type amides with arylboronic esters
to deliver diarylketones.25 As a continuation of those studies,
we set to investigate the nickel‐catalyzed alcoholysis of N‐
acyloxazolidin‐2‐ones, and report herein the results.26
a Reaction conditions: 1a, 0.12 mmol; MeOH, 0.144 mmol (1.2 equiv); toluene,
0.25 M; 80 ºC ;12 h; b Yield determined by 1H NMR spectroscopy using 1,3,5‐
trimethoxybenzene as an internal standard; c Isolated yield; d Ni(cod)2: 5 mol%;
2,2’‐bipyr.: 10 mol%; Reaction temperature: 25 ºC; Toluene: 0.80 M;
MeOH: 1.5 equiv.
e
f
g
yields (17‐34%) were obtained with phosphine ligands and BOX
[bis(oxazoline)] ligands (Table 1, entries 1‐5), NHCs such as SIPr,
IPr, SIMes, and IMes turned out to be effective ligands for the
Ni(cod)2‐catalyzed methanolysis reaction (Table 1, entries 6‐9).
Despite the effectiveness of the Ni(cod)2‐NHC combination, the
drawbacks associated with NHC ligands, including low stability,
low atom‐economy, multi‐step preparation, and high price,
prompted us to search for a cheaper while equally effective
ligand. In this regard, 1,10‐phenanthroline appeared to be
promising (entry 10). Best result was obtained from the
combination of Ni(cod)2 with structurally simple, cheap and
easily available 2,2'‐bipyridine (2,2'‐bipyr.), which afforded the
desired ester 3a in 95% yield (Table 1, entry 11). Interestingly,
We opted for 1a as a model compound to investigate the
reaction. A quick survey of catalytic systems showed that no
reaction took place in the absence of a catalyst, neither in the
presence of several Pd and Ni‐catalytic systems (Table ESI‐1,
2 | J. Name., 2012, 00, 1‐3
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the NiCp2/2,2'‐bipyr. catalyst system also furnished ester 3a in corresponding N‐acyloxazolidinones by alkylation.7 Catalytic
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DOI: 10.1039/C7GC03534A
88% yield (Table 1, entry 12). To our satisfaction, reducing alcoholysis of N‐acyloxazolidinone 2a proceeded smoothly to
equivalents of Ni(cod)2 from 10 mol% to 5 mol%, yield of the give methyl (S)‐2‐methyl‐3‐phenylpropanoate (3j) in 85% yield.
methanolysis was unaffected (96%)(Table 1, entry 13). After Taking into account that the starting 2a used being an
defining the optimal catalyst system, effects of solvent (see inseparable diastereomeric mixture in
a 98: 2 ratio,
Table ESI‐2, entries 10‐13), reaction temperature (Table 1, racemization is less than 1% during the reaction (assuming that
entries 14), concentration (Table 1, 15), amount of catalyst and N‐acyloxazolidinones are enantiopure). Methanolysis of allylic
ligand (Table ESI‐3), and equivalents of methanol (Table ESI‐4) and propargylic derivatives 2b and 2c led to methyl esters 3k
were examined, and the optimal conditions were established as: and 3l in 88% and 82% yield, respectively. Catalytic alcoholysis
in the presence of 5 mol% of Ni(cod)2, 10 mol% of 2,2'‐bipyridine, of cis‐1‐amino‐2‐indanol derived imide 2d also proceeded
treating N‐acyloxazolidinone 1a with 1.5 equiv of MeOH at rt smoothly to give ester 3j in 89% yield. Next, we examined the
(Table 1, entry 16).
methanolysis of 2‐phenylpropanimides 2e‐2g, a sub‐class of
Under the optimized conditions, scope of N‐acyloxazolidin‐2‐ substrates known to be highly prone to racemization.13a The
ones was surveyed (Table 2). An examination of achiral N‐ alcoholysis reactions yielded in 82‐90% yields. In all cases,
acyloxazolidinones showed that the reaction worked well with racemization were less than 2%. Similarly, methanolysis of 2h
oxazolidinones bearing N‐aliphatic acyl
unsaturated acyl (1d), N‐aromatic acyl (1e
(
1a
‐
1c), N‐

,

‐
gave 3o in 83% yield with only 1.1% racemization. The reaction
,
1f), electron‐rich tolerated both electron‐withdrawing (2i) and electron‐donating
heteroaromatic acyl (1g
aromatic acyl groups (1i), providing the corresponding methyl 3p and 3q. For substrate 2j, a higher loading of the catalyst
esters 3a 3i in 88–92% yields (Table 2, entries 1‐9). Significantly, Ni(cod)2 enhanced the reaction, giving a better yield. To
, 1h), as well as electron‐deficient groups (2j), delivering the corresponding methanolysis products
–
the catalytic alcoholysis of (S)‐phenylglycinol‐derived N‐ demonstrate that the chiral auxiliary can be recycled, we
acyloxazolidinone 1j, a sterically hindered substrate, also recovered chiral auxiliary 4c in 85% yield from the reaction of
proceeded smoothly to afford methyl ester 3a in 91% yield 2e (Table 3, entry 5). Its optical rotation data: [α]D20 + 5.1 (c 1.05,
(Table 2, entry 10), along with recovered chiral auxiliary 4b in EtOH) is comparable with that reported in the literature (ref.
90% yield. To the best of our knowledge, catalytic alcoholysis of 21b): [α]D + 4.9 (c 1.1, EtOH) for >99%ee.
hindered N‐acyloxazolidinones derived from phenylglycinol After examining the asymmetric alkylation products, we
have not been reported.
proceeded to investigate the alcoholysis of N‐acyloxazolidinone
Encouraged by these results, we next focused on the alcoholysis derivatives prepared by Diels‐Alder reaction (2k, Table 4),
of chiral N‐acyloxazolidinones (Table 3). For this purpose, N‐ asymmetric Michael addition (2l), tandem asymmetric Michael
acyloxazolidinone derivatives 2a‐2j were prepared from the
addition‐‐alkylation (2m), and asymmetric aldol addition
reaction (2n‐2p)9 (Table 4). The Diels‐Alder adduct 2k worked
well under the established conditions, giving the methyl ester
3r in 84% yield. Methanolysis of the asymmetric Michael
addition product 2l produced chiral ester 3s in 83% yield. For
Table 2 Scope of the methanolysis of N‐acyloxazolidinonesa
sterically more hindered asymmetric Michael addition‐‐
methylation product 2m, methanolysis gave methyl ester 3t in
57% yield, which was slightly improved to 65% when IMes was
used as a ligand. Moreover, unprotected asymmetric aldol
adduct 2n underwent smooth catalytic alcoholysis to deliver
ester 3u in excellent yield. The reaction of furan‐2‐yl derivative
afforded methyl ester 3v in 85% yield. Hindered aldol adduct
bearing a naphthalen‐1‐yl group 2p also reacted to yield methyl
ester 3w albeit in a modest yield (63%).
Entry Substrate
R1
R2
Yield (%)b
1
2
1a
1b
1c
1d
1e
1f
Bn
Ph(CH2)2
n‐C11H23
(E)‐PhCH=CH
Ph
H
H
3a: 92
3b: 88
3c: 90
3d: 85
3e: 91
3f: 90
3g: 88
3h: 89
3i: 90
3
H
H
To further extend scope of the reaction, we addressed the
catalytic alcoholysis using other alcohols than methanol (Table
5). When ethanol was used as an alcoholysis reagent, the
4
H
H
H
H
H
5
reactions of 1b 1f proceeded at 80
,
1d
‐
C for 12 h to give
6
2‐naphthyl
2‐furyl
aromatic (3x 3y), ,‐unsaturated (3z) or aliphatic (3aa) ethyl
,
7
1g
1h
1i
esters in good yields (80‐85%) (Table 5, entries 1‐4). Benzyl
esters, being convertible to the corresponding carboxylic acid
by mild catalytic hydrogenolysis,16,27 are synthetically more
useful. However, catalytic benzylolysis of N‐acyloxazolidinones
is scarce and requires the use of either a large excess of (10 – 50
equiv) of benzyl alcohol or 1.0 equiv. of catalyst.16,18 In our case,
under the established conditions, benzyl ester 3ab was
obtained in 76% yield from 1e (Table 5, entry 5). The Diels‐Alder
adduct 2k also reacted smoothly, providing the benzyl ester 3ac
8
2‐thienyl
3,4‐Cl‐Ph
Bn
9
10
1j
Ph (S)
3a: 91c
a
Reaction conditions: 1a‐1j, 0.40 mmol; MeOH, 0.60 mmol (1.5 equiv);
toluene, 0.80 M; 25 ºC, 12 h ; b Isolated yield; c Chiral auxiliary 4b recovered in
90% yield.
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Table 4 Scope of substrates from diverse asymmetric reactionsa
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DOI: 10.1039/C7GC03534A
Table 3 Scope of the substrate obtained from asymmetric alkylationa
Entry Substrate/ Product (yield)b Entry
Substrate/ Product (yield)b
Substrate (dr)b/
Substrate (dr)b/
Product (yield,c eed
(stereoselectivity)e
En
try
Entry
Product (yield,c eed
(stereoselectivity)e
OH
O
O
N
O
1
4
Me
Bn
2k/ 3r (84%)
2l/ 3s (83%)
2n/ 3u (92%)
1
6
2a (98:2 dr) /
3j, 85%, 94.3% ee (99.1%)
2f (99:1 dr) /
3m, 88%, 97.4% ee (99.0%)
2
3
5
6
2o/ 3v (85%)
2p/ 3w (63%)
2
3
7
8
2g (95:5 dr) /
3n, 88%, 86.5% ee (98.2%)
2b (99:1dr) /
3k, 88%, 97.9% ee (99.4%)
2m/ 3t (57%c, 65%d)
a
Reaction conditions: 2k‐2p, 0.30 mmol; MeOH, 0.45 mmol (1.5 equiv);
toluene, 0.80 M; 25 ºC, 12 h ; b Isolated yield;c Reaction temperature: 80 ºC; d
Ligand: IMes (10 mol%), 80 ºC.
in 76% yield (entry 6). Furthermore, the catalytic alcoholysis of
chiral N‐acyloxazolidinone 2e and 1k with benzyl alcohol
produced the benzyl ester 3af and 3ae in good to excellent
yields (entries 7 and 8). The alcoholysis of 1a with secondary
alcohols cyclohexanol and isopropanol afforded the
corresponding esters in moderate yields (55% and 62%, entries
9 and 10). Attempted alcoholysis of more hindered tert‐butanol
produced the corresponding ester in less than 5% yield with
most of the starting material recovered.
2c (98:2 dr) /
3l, 82%, 95.6% ee (99.6%)
2h (88:12 dr) /
3o, 83%, 74.4% ee (98.9%)
4
9
2i (99:1 dr) /
3p, 88%, 99.0% ee (>99.0%)
2d (98:2 dr) /
3j, 89%, 93.8% ee (99.0%)
To demonstrate the value of our method, the enantioselective
synthesis of 9, the C22‐C26 segment (9) of a close analogue of
the potent immunosuppressant agent FK50628 was conducted
(Scheme 3). Subjecting of 529 to our newly developed Ni‐
catalyzed methanolysis conditions, run at a gram‐scale,
afforded methyl ester
ester with enolate generated in situ from t‐butyl acetate gave
‐ketoester in 88% yield. Stereoselective reduction of by
Prasad’s method30 produced the all‐cis diastereomer
as a
single diastereomer in 90% yield.Treatment of with 2 NaOH
in methanol provided the desired ‐hydroxy‐ ‐lactone in 80%
6 in 61% yield. Condensation of methyl
5
10
6
2e (97:3 dr) /
3m, 90%, 92.3% ee (98.9%)
Recovered 4c [R3 = (S)‐Bn],
85% f

7
7
2j (99:1 dr) /
8
3q, 72%, g 95.1% ee (99.0%)
8
M


9
a
Reaction conditions: 2a‐2j, 0.30 mmol; MeOH, 0.45 mmol (1.5 equiv);
toluene, 0.80 M; 25 ºC; 12 h; b Diastereomeric ratios of 2a‐2j were determined
by 1H NMR; c Yield of isolated product; d Enantiomeric excesses of 3j‐3q were
determined by HPLC (see ESI); e Stereoselectivity of the reaction calculated by
[100 × er of 3 / (dr of 2]; f Recovered chiral auxiliary 4b: [α] D + 5.1 (c 1.05,
EtOH), lit [α] D + 4.9 (c 1.1, EtOH) for > 99% ee21b g Ni(cod)2, 10 mol%.
;
yield. Lactone
FK506.28
9
has been integrated into an analogue of
20
4 | J. Name., 2012, 00, 1‐3
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Table 5 Catalytic alcoholysis of N‐acyloxazolidinones with other alcohols a
alcoholysis with other alcohols), the reaction displayed
excellent chemoselectivity, good functional group tolerance,
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DOI: 10.1039/C7GC03534A
Ent
ry
Substrate/
Product (yield)b
En
try
Substrate/
Product (yield)b
R3
Et
R3
1
2
3
4
6
7
8
9
Bn
2k/ 3ac (76%)
2e/ 3ad (75%)
1e/ 3x (85%)
Et
Et
Et
Bn
Bn
Scheme 2 Asymmetric synthesis of δ‐lactone 9.
1f/ 3y (82%)
1d/ 3z (80%)
and the chiral auxiliary can be recycled readily. Less than 1%
racemization was observed for substrates bearing epimerizable
chiral center, even for racemization‐prone substrates,
racemization was less than 2%. The method is versatile for N‐
acyloxazolidinones prepared from different asymmetric
reactions that cover challenging aldol adducts and hindered N‐
acyloxazolidinones derived from phenylglycinol. Synthetically
more useful yet more challenging alcoholysis using benzyl
alcohol as a nucleophile can also be achieved. The yields were
good to excellent for most substrates, and the reaction could be
run at gram‐scale. The successful application of the new
methodology to the synthesis of the C22‒C26 segment of a
close analogues of the immunosuppressant agent FK506 will
stimulate its application for the synthesis of other natural
products and medicinal agents. Further expansion of this
methodology is currently ongoing in our laboratory and the
results will be reported in due course.
1k/ 3ae (93%)
1a/ 3af (55%)
c‐hex
1b/ 3aa (81%)
1e/ 3ab (76%)
5
Bn
10
i‐Pr
1a/ 3ag (62%)
a Reaction conditions: 1b, 1d‐1f, 2k, 2e, 1k, , 0.30 mmol; R3OH, 0.45 mmol (1.5
equiv); toluene, 0.80 M; 80 ºC; 12 h ; b Isolated yield.
ConflEicts of interest
t
There are no conflicts to declare.
Conclusions
Acknowledgements
In summary, we have achieved the first earth‐abundant and
cheap transition metal‐catalyzed alcoholysis of N‐
acyloxazolidinones to deliver esters, a key transformation for
the application of the powerful N‐acyloxazolidinone‐based
platform for asymmetric synthesis. The combination of cheap
Ni
metal with structurally simple, cheap and easy to handle 2,2'‐
bipyridine as an effective ligand, and only 1.5 equivalents of the
alcohol nucleophile used, rend the method expedient,
economical and sustainable. Running under exceptionally mild
The authors are grateful for financial support from the National
Key R&D Program of China (grant No. 2017YFA0207302), the
National Natural Science Foundation of China (21332007 and
21672176) and the Program for Changjiang Scholars and
Innovative Research Team in University of Ministry of Education,
China.
Notes and references
conditions (room temperature for methanolysis, and 80 C for
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1
(a) S. L. Y. Tang, R. L. Smith and M. Poliakoff, Green Chem., 20 (a) Y. K. Wu, Y. Q. Yang and Q. Hu, J. Org. CheVmie.w, A2rt0ic0le4O,n6lin9e
,
2005,
7
, 761; (b) P. T. Anastas and J. C. Warner, Green
3990; for an application of the latter method, see: (b) Y. Wu
Chemistry: Theory and Practice, Oxford University Press, 1998.
and Y.‐P. Sun, J. Org. Chem., 2006, 71,D5O74I:810. .1039/C7GC03534A
2
3
(a) B. M. Trost, Science, 1991, 254, 1471; (b) C.‐J. Li and B. M. 21 (a) S. Oishi and S. Saito, Angew. Chem. Int. Ed., 2012, 51, 5395;
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Green Chemistry
View Article Online
DOI: 10.1039/C7GC03534A
Ni-Catalyzed Chemoselective Alcoholysis of N-Acyloxazolidinones
Pei-Qiang Huang,* and Hui Geng
We report the first Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver
esters.
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