Facile Domino Access to Chiral Bicyclo[3.2.1]octanes and Discovery of a New Catalytic Activation Mode

被引：108

作者：

Tan, Bin ^{[1
]}

Lu, Yunpeng ^{[1
]}

Zeng, Xiaofei ^{[1
]}

Chua, Pei Juan ^{[1
]}

Zhong, Guofu ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

关键词：

MICHAEL-ALDOL REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOCENTERS; HENRY REACTION; MULTISUBSTITUTED CYCLOPENTANES; CONJUGATE ADDITION; CINCHONA ALKALOIDS; ORGANIC-CHEMISTRY;

D O I：

10.1021/ol1007795

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantio- and diastereoselective organocatalytic domino Michael Henry process for the preparation of synthetically unique and medicinally important bicyclo[3.2.1]octane derivatives with four stereogenic centers including two quaternary stereocenters has been developed. Theoretical OFT calculations on the transition states have been carried out to reveal origins of the excellent stereoselectivities. A novel dual model was thus proposed.

引用

页码：2682 / 2685

页数：4

共 77 条

[1] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[2] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[3] Origins of opposite absolute stereloselectivities in proline-catalyzed direct Mannich and aldol reactions [J].

Bahmanyar, S ;

Houk, KN .

ORGANIC LETTERS, 2003, 5 (08) :1249-1251

[4] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[5] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus [J].

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :42-47

[6]

BUCHI G, 1977, J AM CHEM SOC, V99, P8073

[7] Organocatalytic asymmetric synthesis of α,α-disubstituted α-amino acids and derivatives [J].

Cabrera, Silvia ;

Reyes, Efraim ;

Aleman, Jose ;

Milelli, Andrea ;

Kobbelgaard, Sara ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) :12031-12037

[8] An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons [J].

Cao, Chun-Li ;

Zhou, You-Yun ;

Zhou, Jian ;

Sun, Xiu-Li ;

Tang, Yong ;

Li, Yu-Xue ;

Li, Guang-Yu ;

Sun, Jie .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (42) :11384-11389

[9] A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].

Carlone, Armando ;

Cabrera, Silvia ;

Marigo, Mauro ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104

[10] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].

Chen, Xiao-Hua ;

Wei, Qiang ;

Luo, Shi-Wei ;

Xiao, Han ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825

← 1 2 3 4 5 6 7 8 →