Rhodium-Catalyzed Domino Enantioselective Synthesis of Bicyclo[2.2.2]lactones

被引：36

作者：

Boyer, Alistair ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 32期

基金：

加拿大自然科学与工程研究理事会;

关键词：

asymmetric catalysis; domino reactions; lactones; oxidation; rhodium; RING-OPENING REACTIONS; TRANSITION-METAL CATALYSIS; OXABICYCLIC ALKENES; ALLYLIC ALCOHOLS; REGIODIVERGENT RESOLUTION; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; NUCLEOPHILES; ISOMERIZATION; SUBSTRATE;

D O I：

10.1002/anie.201101773

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Once, twice, three times a catalyst! A novel domino rhodium(I)-catalyzed asymmetric transformation of substituted oxabicyclic alkenes into bicyclo[2.2.2]lactones proceeded with good yields (up to 78 %) and excellent stereoselectivity (>97 % ee; see scheme; cod=1,5-cyclooctadiene, Tf=trifluoromethanesulfonyl). Mechanistic investigations suggest that this process proceeds by rhodium-catalyzed asymmetric ring opening, allylic alcohol isomerization and oxidation. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7346 / 7349

页数：4

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