A new synthetic route for the synthesis of enantioenriched 1,2,3,4-tetrahydronaphthalene-derived 1,3-diols

Article abstract of DOI:10.1080/00397911.2018.1502783

In this report, we presented a new approach to access a (1,3-butadiene-2-yl)carbinol, (1R,2R)- and (1S,2S)-1-(hydroxymethyl)-1-vinyl-1,2,3,4-tetrahydronaphthalene-2-ols. Starting from commercially available 1,4-diol-2-butyne, a six-step synthesis involving dibromination, Zn-mediated addition reaction of phenylpropyl aldehyde, epoxidation, epoxy–arene cyclization, and resolution with D(+)-Camphor afforded the title compounds.

Full text of DOI:10.1080/00397911.2018.1502783

Synthetic Communications
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A new synthetic route for the synthesis of
enantioenriched 1,2,3,4-tetrahydronaphthalene-
derived 1,3-diols
Feng Cheng, Chen Cai, Xing Yang, Zi-Wei Lin, Xiao-Song Hu & Yi-Yong Huang
To cite this article: Feng Cheng, Chen Cai, Xing Yang, Zi-Wei Lin, Xiao-Song Hu
& Yi-Yong Huang (2018): A new synthetic route for the synthesis of enantioenriched
1,2,3,4-tetrahydronaphthalene-derived 1,3-diols, Synthetic Communications, DOI:
10.1080/00397911.2018.1502783
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https://doi.org/10.1080/00397911.2018.1502783
A new synthetic route for the synthesis of enantioenriched
1,2,3,4-tetrahydronaphthalene-derived 1,3-diols
Feng Chengaꢀ Chen Caibꢀ Xing Yangb, Zi-Wei Linb, Xiao-Song Hub, and
Yi-Yong Huangb
aSchool of Materials Science and Engineering, Wuhan University of Technology, Wuhan, P.R. China;
bDepartment of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan
University of Technology, Wuhan, P.R. China
ABSTRACT
ARTICLE HISTORY
Received 17 June 2018
In this report, we presented a new approach to access a (1,3-butadi-
ene-2-yl)carbinol, (1R,2R)- and (1S,2S)-1-(hydroxymethyl)-1-vinyl-1,2,
3,4-tetrahydronaphthalene-2-ols. Starting from commercially available
KEYWORDS
Asymmetric synthesis; 1,3-
diene; 1,3-diol; oxetane
1,4-diol-2-butyne,
a six-step synthesis involving dibromination,
Zn-mediated addition reaction of phenylpropyl aldehyde, epoxidation,
epoxy–arene cyclization, and resolution with D(þ)-Camphor
afforded the title compounds.
GRAPHICAL ABSTRACT
We herein presented a new approach to access a (1,3-butandien-2-
yl)carbinol, (1R,2R)- and (1S,2S)-1-(hydroxymethyl)-1-vinyl-1,2,3,4-tetra-
hydronaphthalen-2-ols.
Introduction
Chiral 1,3-diol motif exists extensively in a variety of pharmaceutical and biologically
active molecules.[1] It has been widely reported that chiral 1,3-diols, the same as 1,2-
and 1,4-diols, play an important role in organic synthesis:[2] (1) working as synthons to
construct complex compounds; (2) acting as chiral ligands or catalysts in asymmetric
CONTACT Yi-Yong Huang
huangyy@whut.edu.cn
Department of Chemistry, School of Chemistry, Chemical
Engineering and Life Science, Wuhan University of Technology, Wuhan, P.R. China.
ꢀThese authors contributed equally.
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.
Supplemental data for this article can be accessed on the publisher’s website.
ß 2018 Taylor & Francis

2
F. CHENG ET AL.
synthesis;[3] (3) using as chiral resolving agents to separate racemic compounds.
Therefore, the synthesis of novel chiral 1,3-diol compounds represents an important
task for organic chemists. Thus far, a lot of synthetic methods have been documented
including enantioselective reductions of b-hydroxyl ketones[4] and 1,3-diketones,[5] cas-
cade reactions initiated from asymmetric aldol reactions,[6] and so on.[7]
In 2015, a chiral 1,3-diol (1S,2S)-1 featuring a tetrahydronaphthalene backbone was
serendipitously obtained from a chiral 1,3-butadienyl-2-carbinol by our group.[8] We
envisaged that the 1,3-diol would be potentially used as a chiral ligand, catalyst, or syn-
thetic precursor. However, the previous synthetic route reported by us has several syn-
thetic limitations: (1) the use of chiral phosphoric acid and anhydrous t-butyl
hydroperoxide (TBHP) is cost-consuming; (2) 93% ee of (1S,2S)-1 is not satisfactory for
being a chiral ligand or catalyst. Toward addressing these issues and creating a reliable
and practical synthetic method to generate chiral (1S,2S)-1 and (1R,2R)-1 in a large-
scale manner, we started to launch this project and reported the details herein.
Discussion
In order to establish an economical, efficient, and easily-handled synthetic route to get
both (1R,2R)-1 and (1S,2S)-1, a six-step synthesis starting from 2-butyne-1,4-diol 2 was
designed (Scheme 1). The first task was to seek for a useful way to get (1,3-butadiene-2-
yl)carbinol rac-5, which is an important type of building block in total synthesis.[9]
They could be generally accessed through the addition reaction of aldehydes with vari-
ous unsaturated reagents.[10] For instance, the pioneering work of creating a protocol of
using 1-trimethylsilyl-2,3-butadiene reagent in the presence of TiCl4-catalyst was
reported by Hatakeyama,[10a] as well as Brown et al. established the non-catalytic add-
ition reaction between aldehydes and homoallenylated boronates.[10b] In 1999, the
Scheme 1. Synthetic route to (1R,2R)-1 and (1S,2S)-1. Reagents and conditions: (a) PBr3, pyridine,
Et2O, 0–40 ꢁC, 89%. (b) Zinc, THF, r.t., 52%. (c) VO(OiPr)3, 6, TBHP (70% aq.), CH2Cl2, r.t., 60%. (d)
Zn(NTf2)2, CH2Cl2, r.t., 75%. (e) p-TsOH, D(þ)-Camphor, benzene, reflux, 100% conversion. (f) p-TsOH,
CH2Cl2/H2O, 85–87%.

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3
catalytic asymmetric dienylation of aldehydes using buta-2,3-dienylstannane was devel-
oped by Hatakeyama and Yu independently.[10c,d] The enantioselective synthesis of (1,3-
diene-2-yl)carbinols by employing homoallenylbromide with a chiral CrIII-catalyst was
achieved by Yamamoto et al.[10e] Miscellaneous other synthetic methods including using
1,3-butadiene-2-yl organometallic reagents,[11] ethylene-alkyne cross-metathesis with
propargyl alcohols,[12] tandem alkylbromide-epoxide vinylations using dimethylsulfo-
nium methylide,[13] and cascade allenylation/desilylation/isomerization[14] were also
illustrated. In view of easy availability of starting materials and large-scale synthesis of
(1,3-butandien-2-yl)carbinol products, Chan’s method involving using 1,4-dibromo-2-
butyne reagent and aldehydes was considered to be more promising than the above-
listed methods.[15] However, the key issue of Chan’s work is the use of stoichiometric
amount of expensive In(0) metal. Considering cheap Zn(0) metal bearing similar chem-
ical property to In(0) metal in Barbier-type reaction, we hoped Zn(0) could replace
In(0) to mediate the 1,3-butadiene-2-ylation of aldehydes. The optimization of the reac-
tion condition was shown in Table 1. Compound 3 was easily accessible through the
dibromination of commercially available 1,4-diol-2-butyne. According to Chan’s meth-
od,[15a] the transformation of compound 3 and phenylpropyl aldehyde 4 in aqueous
media proceeded in only 25% yield (entry 1, Table 1). The replacement of In(0) to
Zn(0) could not deliver any desired product (entry 2). The use of organic solvents, such
as DMF, Et2O, and THF (entries 3–5), was essential for the reaction mediated by Zn(0),
and up to 36% yield was obtained in THF at 25 ꢁC. Anhydrous THF improved the yield
to 52%, which could be understood in the plausible mechanism (Figure 1). In the pres-
ence of trace amount of water, hydrolysis of organozinc intermediate I may occur to
lead to undesired reaction pathway. The addition of propargyl intermediate I to alde-
hyde 4 provides allenyl intermediate II, which undergoes the second oxidative insertion
of Zn(0) to afford homoallenyl organozinc intermediate III. After the reaction, workup
of the reaction mixture with saturated aqueous NH4Cl gave the desired (1,3-butadiene-
2-yl)carbinol rac-5.
Table 1. Optimization of reaction conditions for 3 and 4.
Entry
Metala
T/oC
Solvent
Yield/%
1
2
3
4
In
25
25
25
25
25
25
50
H2O
H2O
DMF
Et2O
THF
THF
THF
25
Trace
20
13
36
52
15
Zn
Zn
Zn
Zn
Zn
Zn
5
6b
7b
aZn was activated with diluted HCl (aq.). bAnhydrous THF was used.
Figure 1. Plausible reaction mechanism for the transformation of 3 to rac-5.

4
F. CHENG ET AL.
Scheme 2. Synthetic utility of chiral 1,3-diol (S,S)-1.
With rac-5 in hand, we continued to study the epoxidation of the allylic alcohol at
low cost. Expensive anhydrous TBHP reagent was usually utilized as an oxidizing
reagent in Sharpless-epoxidation reactions.[16] The Yamamoto group paved the way to
employ cheap aqueous TBHP reagent.[17] Inspired by this work, we carried out the
non-asymmetric variant by using easily-prepared hydroxamic acid 6 as a racemic ligand.
As expected, rac-erythro-7 was readily obtained in 60% yield when injecting 70% aq.
TBHP reagent, which facilitated the 6-exo-tet epoxy–arene cyclization to provide rac-cis-
1 according to our previously identified procedure.[8]
The final task was how to resolve 1,3-diol rac-cis-1. Initial attempts of using various
common chiral resolving reagents via non-covalent interactions, such as L-Proline,
(þ)-1-benzylcinchonanium chloride and (R)-(þ)-1-phenylethylamine, were failed even
by changing a wide array of solvents. To our delight, two ketal diastereoisomers 8a and
8b formed from rac-cis-1 and D(þ)-Camphor were successfully separated by using sil-
ica-gel column chromatography. Consequently, 8a and 8b were hydrolyzed to give both
target enantiomers (1R,2R)-1 and (1S,2S)-1 with 95% ee, which was recrystallized once
in petroleum ether/ethyl ether to give two enantiomers with 99% ee (85–87% yields).
The absolute configuration of (R,R)-1 was well determined by single crystal X-ray dif-
fraction (see SI; CCDC 1552373 ((R,R)-1) contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge from The Cambridge
Crystallographic Data Centre).
The synthetic utility of (1S,2S)-1 was demonstrated in Scheme 2. Selective tosylation
of the primary alcohol for (1S,2S)-9 was achieved based on the reactivity difference
between the two hydroxyl groups. Under basic condition, 1,2,3,4-tetrahydronaphtha-
lene-derived oxetane (1S,2S)-10 was successfully built in 62% yield, which is regularly
embedded as a key motif in natural products, such as paclitaxel.[18]
In this report, we mainly focused on the updated synthesis of a (1,3-butadiene-2-
yl)carbinol and both enantiomers of 1-(hydroxymethyl)-1-vinyl-1,2,3,4-tetrahydronaph-
thalene-2-ols. The reaction mechanism of the Zn-mediated reaction of phenylpropyl
aldehyde and 1,4-dibromo-2-butyne to form (1,3-butadiene-2-yl)carbinol was proposed.
The synthetically useful pathway features cost-effective and practical. The asymmetric
synthesis of an enantioenriched 1,2,3,4-tetrahydronaphthalene-derived oxetane was
facilitated by the chiral 1,3-diol. Further, synthetic application of the chiral 1,3-diols in
novel chiral ligands and catalysts synthesis are ongoing in our lab.
Experimental sections
Chiral resolution of rac-cis-1
rac-cis-1 (1.0 g, 5.0 mmol), D(þ)-Camphor (2.28 g, 15.0 mmol) and p-TsOHꢂH2O
(19 mg, 0.02 mmol) were refluxed in 30 mL benzene with azeotropic removal of water.

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5
After rac-cis-1 was fully consumed, anhydrous potassium carbonate was added. The
reaction mixture was allowed to stir for 5 min before filtration. The filtrate was concen-
trated under vacuum and the residue was separated on a column of silica gel (pure pet-
roleum ether, Rf = 0.2) to give pure white solid 8a (0.3798 g, 23%) and 8b (0.3614 g,
22%) at the first time. The residue of ketal diastereoisomers was again separated, and
the total yields of 8a and 8b were 45% and 44%, respectively. The ketals 8a and 8b
were readily hydrolyzed in the presence of p-TsOHꢂH2O to give two enantiomers
20
20
(1R,2R)-1 ([a]D ¼ ꢃ5.4
(c ¼ 1.0,
CHCl3))
and (1S,2S)-1 ([a]D ¼ þ5.6
(c ¼ 1.0, CHCl3))[8].
1
8a, 45%: H NMR (500 MHz, CDCl3) d 7.29–7.26 (m, 1H), 7.22–7.11 (m, 3H), 5.76
(dd, 17.5 Hz, 10.5 Hz, 1H), 5.14 (d, 11.0 Hz, 1H), 4.67 (d, 17.5 Hz, 1H), 4.29 (d, 12.0 Hz,
1H), 4.07 (d, 2.5 Hz, 1H), 3.94 (d, 11.5 Hz, 1H), 3.17–3.09 (m, 1H), 2.61 (dd, 16.5 Hz,
6.0 Hz, 1H), 2.22–2.17 (m, 2H), 2.02–1.95 (m, 1H), 1.86–1.78 (m, 3H), 1.70–1.64 (m,
1H), 1.19–1.09 (m, 2H), 1.00 (s, 3H), 0.82 (s, 3H), 0.52 (s, 3H). 13C NMR (126 MHz,
CDCl3) d 141.99, 137.94, 136.31, 128.62, 128.16, 125.73, 125.38, 117.56, 106.88, 71.74,
66.78, 53.44, 47.48, 45.38, 44.10, 38.79, 28.78, 27.13, 24.86, 24.18, 20.79, 20.67, 9.53. mp
=64–65 ꢁC. IR (KBr): 3066.3, 2942.8, 2871.5, 1862.9, 1635.3, 1471.4, 1450.2, 1371.1,
1315.2, 1267.0, 1232.3, 1203.4, 1176.4, 1122.4, 1045.3, 993.2, 929.5, 757.9. HRMS calcd.
20
for [M]þ: 338.2246; found: 338.2236. [a]D ¼ ꢃ73.4 (c ¼ 0.5, CHCl3).
1
8b, 44%: H NMR (500 MHz, CDCl3) d 7.25 (m, 1H), 7.20–7.12 (m, 3H), 5.75 (dd,
17.5 Hz, 11.0 Hz, 1H), 5.13 (d, 11.0 Hz, 1H), 4.67 (d, 17.0 Hz, 1H), 4.17 (d, 12.0 Hz, 1H),
4.02–4.01 (m, 1H), 3.93 (d, 12.0 Hz, 1H), 3.16–3.10 (m, 1H), 2.60 (dd, 16.5 Hz, 6.0 Hz,
1H), 2.17–2.14 (m, 1H), 2.02–1.94 (m, 2H), 1.89–1.85 (m, 1H), 1.79–1.77 (m, 1H),
1.70–1.66 (m, 1H), 1.62–1.57 (m, 1H), 1.20–1.11 (m, 2H), 0.94 (s, 3H), 0.81 (s, 3H),
0.44 (s, 3H). 13C NMR (126 MHz, CDCl3) d 142.02, 137.97, 136.23, 128.71, 128.07,
125.77, 125.50, 117.67, 106.90, 69.29, 53.49, 47.84, 45.23, 44.05, 38.55, 28.36, 27.22,
24.97, 24.31, 20.84, 20.77, 9.39. mp =83–84 ꢁC. IR (KBr): 3060.5, 2925.5, 2865.7, 1857.1,
1591.0, 1479.1, 1450.2, 1380.8, 1317.1, 1263.1, 1197.6, 1122.4, 1047.2, 977.7, 925.7, 757.9.
20
HRMS calcd. for [M]þ: 338.2246; found: 338.2236. [a]D ¼ þ23.4 (c ¼ 1.0, CHCl3).
Funding
We gratefully thank the financial support of this investigation by the National Natural Science
Foundation of China [21573169, 21772151], Natural Science Foundation of Hubei Province
[2018CFA084], and Wuhan Morning Light Plan of Youth Science and Technology
[2017050304010314].
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