89053-64-5Relevant academic research and scientific papers
Preparation and reactions of optically active 4-hydroxy-1,3-dioxolanes: 2-Hydroxy aldehyde equivalents
Kim, Hwa-Ok,Friedrich, Dirk,Huber, Ed,Peet, Norton P.
, p. 3453 - 3469 (1996)
The preparation and reactions of optically and chemically stable (S)-4-hydroxy-1,3-dioxolane 3 as a 2-hydroxy aldehyde equivalent were explored. Hydroxydioxolane 3 was prepared by reduction of ketodioxolane 2 which was obtained from (S)-2-hydroxycarboxyli
Enantioselective synthesis of allenes by catalytic traceless petasis reactions
Jiang, Yao,Diagne, Abdallah B.,Thomson, Regan J.,Schaus, Scott E.
supporting information, p. 1998 - 2005 (2017/02/15)
Allenes are useful functional groups in synthesis as a result of their inherent chemical properties and established reactivity patterns. One property of chemical bonding renders 1,3-substituted allenes chiral, making them attractive targets for asymmetric synthesis. While there are many enantioselective methods to synthesize chiral allenes from chiral starting materials, fewer methods exist to directly synthesize enantioenriched chiral allenes from achiral precursors. We report here an asymmetric boronate addition to sulfonyl hydrazones catalyzed by chiral biphenols to access enantioenriched allenes in a traceless Petasis reaction. The resulting Mannich product from nucleophilic addition eliminates sulfinic acid, yielding a propargylic diazene that performs an alkyne walk to afford the allene. Two enantioselective approaches have been developed; alkynyl boronates add to glycolaldehyde imine to afford allylic hydroxyl allenes, and allyl boronates add to alkynyl imines to form 1,3-alkenyl allenes. In both cases, the products are obtained in high yields and enantioselectivities.
Two-carbon-elongated HIV-1 protease inhibitors with a tertiary-alcohol- containing transition-state mimic
Wu, Xiongyu,?hrngren, Per,Ekegren, Jenny K.,Unge, Johan,Unge, Torsten,Wallberg, Hans,Samuelsson, Bertil,Hallberg, Anders,Larhed, Mats
, p. 1053 - 1057 (2008/09/20)
A new generation of HIV-1 protease inhibitors encompassing a tertiary-alcohol-based transition-state mimic has been developed. By elongation of the core structure of recently reported inhibitors with two carbon atoms and by varying the P1′ group of the co
HIV protease inhibitors
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Page/Page column 102, (2008/06/13)
Compounds of the formula (I): Wherein R1, R2, X and N are as defined in the specification; E is N, CH; A1 and A" are terminal groups as defined in the specification. The compounds have utility as HIV-I protease inhibitors.
Two complementary approaches toward 2-alkoxy carboxylic acid synthesis from 1,3-dioxolan-4-ones
Winneroski, Leonard L.,Xu, Yanping
, p. 4948 - 4953 (2007/10/03)
Two complementary approaches to prepare 2-alkoxy carboxylic acids have been developed. Reductive ring opening of various 1,3-dioxolan-4-ones using TiCl4/Et3SiH or tBuMgCl affords the desired 2-alkoxy carboxylic acid in mod
Diastereoselective synthesis of protected 2,3-dihydroxynitriles from 2- hydroxy acids
Hutin, Pierre,Larchevêque, Marc
, p. 220 - 222 (2007/10/03)
The DIBAL-H reduction of dioxolanones 2 prepared from 2-hydroxy acids followed by addition of acetone cyanohydrin affords the syn 2,3- dihydroxynitriles in high enantiomerical purities.
OPTICAL ACTIVITY OF LACTONES AND LACTAMS-I; CONFORMATIONAL DEPENDENCE OF THE CIRCULAR DICHROISM OF 1,3-DIOXOLAN-4-ONES
Polonski, T.
, p. 3131 - 3137 (2007/10/02)
Several optically active 1,3-dioxolan-4-ones were synthesized from corresponding α-hydroxy acids.The Cotton effect sign of these compounds can be explained by Weigans's sector rules.The existence of an equilibrium between envelope and planar conformations
