Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions

被引：74

作者：

Futatsugi, K ^{[1
]}

Yamamoto, H ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 10期

关键词：

asymmetric catalysis; cycloaddition; Diels-Alder reaction; Lewis acids;

D O I：

10.1002/anie.200461319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactive, selective, and tough, the chiral Lewis acid generated from 1 and SnCl4 catalyzes the enantioselective Diels-Alder reactions of various classes of substrates (see scheme). The reactive species preserves its asymmetric induction ability even in the presence of a large excess of SnCl 4. Importantly, this catalyst system is tolerant to a small amount of moisture, oxygen, and Lewis bases. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1484 / 1487

页数：4

共 65 条

[1] REARRANGEMENTS IN LEWIS ACID-CATALYZED DIELS-ALDER REACTIONS - ROUTE TO SUBSTITUTED BICYCLO[2.2.1]HEPTANONES
BALDWIN, JE
LUSCH, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12) : 1923 - 1927
[2] BAO J, 1998, J AM CHEM SOC, V120, P8271
[3] Corey E.J., 2002, ANGEW CHEM, V114, P1724, DOI DOI 10.1021/JACS.7B06567
[4] Corey E. J., 1998, ANGEW CHEM, V110, P402
[5] Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
[6] 2-B
[7] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[8] 2-Z
[9] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[10] 2-V

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