A Highly Enantioselective Catalytic Mannich Reaction of Indolenines with Ketones

被引：22

作者：

Cheng, Dao-Juan ^{[1
]}

Tian, Shi-Kai ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Chinese Acad Sci, Key Lab Synthet Chem Nat Subst, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 09期

基金：

中国国家自然科学基金;

关键词：

enantioselectivity; indolenines; ketones; Mannich reaction; regioselectivity; ASYMMETRIC-SYNTHESIS; IMINES; REARRANGEMENT;

D O I：

10.1002/adsc.201300161

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A range of polysubstituted indolenines (3H-indoles) smoothly underwent an L-proline-catalyzed enantioselective Mannich reaction with various ketones in a highly regioselective manner to give structurally diverse 2-acylmethylindolines in good yields with excellent ee. The current study provides a powerful approach for the transformation of unactivated five-membered cyclic aldimines into optically active nitrogen-containing heterocycles with high enantioselectivity.

引用

页码：1715 / 1718

页数：4

共 34 条

[1] [Anonymous], 2012, ANGEW CHEM INT ED, V51, P1191
[2] [Anonymous], 2008, ANGEW CHEM INT ED, V47, P9985
[3] [Anonymous], 2004, ANGEW CHEM INT ED, V43, P4476
[4] Catalytic Asymmetric Synthesis of Dihydroquinazolinones from Imines and 2-Aminobenzamides
Cheng, Dao-Juan
Tian, Yu
Tian, Shi-Kai
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 995 - 999
[5] Catalytic Asymmetric Pictet-Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines
Cheng, Dao-Juan
Wu, Hai-Bian
Tian, Shi-Kai
[J]. ORGANIC LETTERS, 2011, 13 (20) : 5636 - 5639
[6] The direct catalytic asymmetric Mannich reaction
Córdova, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112
[7] Cuendet M., 2008, MODERN ALKALOIDS, P25
[8] Recent developments in asymmetric catalytic addition to C=N bonds
Friestad, Gregory K.
Mathies, Alex K.
[J]. TETRAHEDRON, 2007, 63 (12) : 2541 - 2569
[9] Catalytic asymmetric direct Mannich reaction: a powerful tool for the synthesis of α,β-diamino acids
Gomez Arrayas, Ramon
Carretero, Juan C.
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (07) : 1940 - 1948
[10] HAHN BT, 2008, ANGEW CHEM, V120, P10134

← 1 2 3 4 →