125637-06-1Relevant articles and documents
Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy to Synthesize Chiral Allylic Alcohols
Liu, Zi,Breit, Bernhard
, p. 300 - 303 (2018)
We achieved the first Rh-catalyzed regio- and enantioselective additions of N-hydroxyphthalimide to allenes. This transformation is accomplished via mild reaction conditions, leveraging on Josiphos SL-J003-2 as a chiral ligand to furnish branched O-allyl compounds in good yields with moderate to excellent enantioselectivities. The substrate scope is broad, and various functional groups are tolerated. The utility of this methodology is elaborated by transformation to allylic alcohols with different functional groups as well as to chiral O-allyl hydroxylamines.
Thiacrown ether as regulator of lipase-catalyzed trans-esterification in organic media: Practical optical resolution of allyl alcohols
Takagi, Yumiko,Teramoto, Jun,Kihara, Hiroshi,Itoh, Toshiyuki,Tsukube, Hiroshi
, p. 4991 - 4992 (1996)
Thiacrown either additive enhanced enantioselectivity in lipase- catalyzed trans-esterification of allyl alcohols. Small amounts of thiacrown ether offered highly enantioselective reaction when 5-phenylpentene-3-ol was subjected to the reaction of Pseudomonas cepacia lipase.
A rational design of phosphonium salt type ionic liquids for ionic liquid coated-lipase catalyzed reaction
Abe, Yoshikazu,Yoshiyama, Kazuhide,Yagi, Yusuke,Hayase, Shuichi,Kawatsura, Motoi,Itoh, Toshiyuki
, p. 1976 - 1980 (2010)
A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated, and very rapid transesterification of secondary alcohols accomplished when IL1-PS was used as catalyst in 2-methoxyethoxymethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) as solvent while perfect enantioselectivity was maintaining. Increased K cat value was suggested to be the most important factor in IL1-PS working the best in [P444MEM][NTf2] solvent. The Royal Society of Chemistry 2010.
Concise, scalable and enantioselective total synthesis of prostaglandins
Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
, p. 692 - 697 (2021/06/01)
Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]
Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs
Wang, Pei,Ma, Guo-Rong,Yu, Sheng-Li,Da, Chao-Shan
supporting information, p. 79 - 86 (2018/12/13)
Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.
Enhanced activity and modified substrate-favoritism of Burkholderia cepacia lipase by the treatment with a pyridinium alkyl-PEG sulfate ionic liquid
Kadotani, Shiho,Nokami, Toshiki,Itoh, Toshiyuki
, p. 441 - 447 (2019/01/04)
Three types of pyridinium salts, i.e., 1-ethylpyridin-1-ium cetyl-PEG10 sulfate (PYET), 1-butylpyridin-1-ium cetyl-PEG10 sulfate (PYBU), and 1-(3-methoxypropyl)pyridin-1-ium cetyl-PEG10 sulfate (PYMP), have been prepared and evaluated for their activation property of Burkholderia cepacia lipase by comparison to the control IL-coated enzymes, 1-butyl-2,3-dimethylimidazolium cetyl-PEG10 sulfate-coated lipase PS (IL1-PS). Among the tested pyridinium salt-coated lipases, the PYET-coated lipase PS (PYET-PS) exhibited the best results; the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, 1-(pyridin-4-yl)ethanol, or 4-phenylbut-3-en-2-ol proceeded faster than those of the IL1-PS-catalyzed reaction while maintaining an excellent enantioselectivity (E > 200). This improved efficiency was found to be dependent on the increased Kcat value.
Compound And Method
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Paragraph 0447-0450, (2015/06/17)
A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is
Enantioselective transformation of allyl carbonates into branched allyl carbamates by using amines and recycling CO2 under iridium catalysis
Zheng, Sheng-Cai,Zhang, Min,Zhao, Xiao-Ming
supporting information, p. 7216 - 7221 (2014/06/23)
Enantioselective transformation of allyl carbonates into branched allyl carbamates by using amines and recycling CO2 in the presence of an Ir complex and K3PO4 was accomplished. This provided branched allyl carbamates in fair to excellent yields with up to 98:2 regioselectivity and 93% ee. The role of CO2 in this transformation is discussed as well.
COMPOUND AND METHOD
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Page/Page column 90, (2014/01/08)
A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO-R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I).
Iterative asymmetric allylic substitutions: Syn- and anti-1,2-diols through catalyst control
Park, Jin Kyoon,McQuade, D. Tyler
supporting information; experimental part, p. 2717 - 2721 (2012/04/17)
A copper-catalyzed asymmetric allylic boronation (AAB) gives access to syn- and anti-1,2-diols. The method facilitates an iterative strategy for the preparation of polyols (see scheme), such as the fully differentiated L-ribo-tetrol and protected D-arabin
