Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH••••O hydrogen bonding

被引：34

作者：

Paddon-Row, Michael N. ^{[1
]}

Kwan, Laurence C. H. ^{[2
]}

Willis, Anthony C. ^{[2
]}

Sherburn, Michael S. ^{[2
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 37期

关键词：

asymmetric catalysis; density functional calculations; Lewis acids; Lewis bases; transition states;

D O I：

10.1002/anie.200802002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7013 / 7017

页数：5

共 50 条

[1] Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding
Thadani, AN
Stankovic, AR
Rawal, VH
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) : 5846 - 5850
[2] Enantioselective Synthesis of Allylic Alcohols via an Oxazaborolidinium Ion Catalyzed Diels-Alder/Retro-Diels-Alder Sequence
Jones, Simon
Valette, Damien
ORGANIC LETTERS, 2009, 11 (22) : 5358 - 5361
[3] 3-(Methoxycarbonyl)Cyclobutenone as a Reactive Dienophile in Enantioselective Diels-Alder Reactions Catalyzed by Chiral Oxazaborolidinium Ions
Yan, Peng
Zhong, Changxu
Zhang, Jie
Liu, Yu
Fang, Huayi
Lu, Ping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (09) : 4609 - 4613
[4] Enantioselective Diels-Alder reactions catalyzed by samarium iodo binaphthoxides
Giuseppone, N
Santos, I
Collin, J
TETRAHEDRON LETTERS, 2000, 41 (05) : 639 - 642
[5] Enantioselective Organocatalytic Diels-Alder Reactions
Merino, Pedro
Marques-Lopez, Eugenia
Tejero, Tomas
Herrera, Raquel P.
SYNTHESIS-STUTTGART, 2010, (01): : 1 - 26
[6] Enantioselective and Structure-Selective Diels-Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules
Corey, E.J. (corey@chemistry.harvard.edu), 1600, American Chemical Society (126):
[7] Hydrogen bonding assisted hetero Diels-Alder reactions.
Huang, Y
Rawal, VH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U42 - U42
[8] Enantioselective rare-earth catalyzed quinone Diels-Alder reactions
Evans, DA
Wu, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) : 10162 - 10163
[9] Mechanistic studies of hydrazide-catalyzed enantioselective Diels-Alder reactions
Lemay, Mathieu
Ogilvie, William W.
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12): : 4663 - 4666
[10] Enantioselective rare-earth catalyzed quinone Diels-Alder reactions
1600, American Chemical Society (125):

← 1 2 3 4 5 →