The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress

被引：455

作者：

Casiraghi, Giovanni ^{[1
]}

Battistini, Lucia ^{[1
]}

Curti, Claudio ^{[1
]}

Rassu, Gloria ^{[2
]}

Zanardi, Franca ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Farmaceut, I-43124 Parma, Italy

[2] CNR, Ist Chim Biomol, I-07100 Sassari, Italy

来源：

CHEMICAL REVIEWS | 2011年 / 111卷 / 05期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC MICHAEL ADDITION; LEWIS-BASE ACTIVATION; MANNICH-TYPE REACTION; ALPHA; BETA-UNSATURATED GAMMA-BUTYROLACTAM; CONJUGATE ADDITION/CYCLIZATION REACTIONS; MGI2-MEDIATED RING EXPANSIONS; HETEROCYCLIC SILYLOXY DIENES; 1,3-BIS(SILYL ENOL ETHERS); CHEMISTRY JOURNAL AWARDEES;

D O I：

10.1021/cr100304n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methodology-oriented and target-oriented researches focused on the various aspects of the vinylogous aldol addition reaction and studies devoted to the related Mannich (VMnR) and Michael (VMcR) processes are summarized. Gademann et al. constructed stereoisomeric seven carbon long galantinic acid substructures during a biomimetic total synthesis of anachelin H, an iron chelator isolated from the cyanobacterium Anabaena cylindrica. Suenaga and co-workers have investigated the stereostructure of Palau'amide by total synthesis, utilizing a VMAR addition as the key step of the entire construction. Kobayashi and co-workers introduced a series of acyclic vinyl ketene silyl N,O-acetals as chiral d4 donor substrates in VMAR processes. Boeckman Jr. et al employed Corey chiral oxazaborolidine to fuel the asymmetric VMAR between silyloxy furan and chiral nonracemic aldehyde.

引用

页码：3076 / 3154

页数：79

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