Catalytic Asymmetric Synthesis of Allylic Alcohols and Derivatives and their Applications in Organic Synthesis

被引:261
作者
Lumbroso, Alexandre [1 ]
Cooke, Michael L. [1 ]
Breit, Bernhard [1 ]
机构
[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany
关键词
allylic alcohols; asymmetric synthesis; natural products; stereoselective catalysis; synthetic methods; DYNAMIC KINETIC-RESOLUTION; HIGHLY ENANTIOSELECTIVE ADDITION; BAYLIS-HILLMAN REACTION; QUATERNARY CARBON CENTERS; CYCLIC ALPHA; BETA-UNSATURATED KETONES; TETHERED AMINOHYDROXYLATION TA; ALDEHYDE OXIDATION LEVEL; ALKYL GRIGNARD-REAGENTS; UNIFIED TOTAL-SYNTHESIS; DIELS-ALDER REACTION;
D O I
10.1002/anie.201204579
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Allylic alcohols represent an important and highly versatile class of chiral building blocks for organic synthesis. This Review summarizes the plethora of methods developed for the catalytic asymmetric synthesis of enantioenriched allylic alcohols. These include: dynamic kinetic resolution (DKR/DKAT), nucleophilic 1,2-addition to carbonyl groups, allylic substitution, oxidation of CH bonds, the addition of Onucleophiles to systems, reduction of unsaturated carbonyl compounds, and an alternative route from enantioenriched propargylic alcohols. Furthermore, these catalytic asymmetric processes are exemplified by their applications in the syntheses of complex molecules such as natural products and potential therapeutic agents.
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页码:1890 / 1932
页数:43
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