Highly Efficient Asymmetric Synthesis of Enantiopure Dihydro-1,2-oxazines: Dual-Organocatalyst-Promoted Asymmetric Cascade Reaction

被引：31

作者：

Lin, Hue ^{[1
]}

Tan, Yu ^{[1
]}

Sun, Xing-Wen ^{[1
]}

Lin, Guo-Qiang ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 15期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; NITROSO ALDOL/MICHAEL REACTION; ENANTIOSELECTIVE SYNTHESIS; ALPHA-AMINOXYLATION; DIASTEREOSELECTIVE SYNTHESIS; ORGANOCASCADE CATALYSIS; ORGANIC CATALYSIS; ENAMINE CATALYSIS; DOMINO REACTIONS; STEREOCENTERS;

D O I：

10.1021/ol301218x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot dual-organocatalyst-promoted asymmetric alpha-aminoxylation/aza-Michael/aldol consendation cascade reaction is presented. The targeted optically active 1,2-oxazine derivatives are synthesized in moderate yields (up to 70%), excellent enantioselectivities (ee >99% in all cases), and excellent diastereoselectivities (dr up to >99:1) under mild conditions. To further elucidate the synthetic utility of the cascade products, cleavage of the N-O bond is demonstrated and an enantiopure syn-1,4-amino alcohol derivative is achieved in excellent yield.

引用

页码：3818 / 3821

页数：4

共 80 条

[11] Asymmetric organocatalytic domino reactions
Enders, Dieter
Grondal, Christoph
Huettl, Matthias R. M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1570 - 1581
[12] Control of four stereocentres in a triple cascade organocatalytic reaction
Enders, Dieter
Hüettl, Matthias R. M.
Grondal, Christoph
Raabe, Gerhard
[J]. NATURE, 2006, 441 (7095) : 861 - 863
[13] Iminium catalysis
Erkkila, Anniina
Majander, Inkeri
Pihko, Petri M.
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5416 - 5470
[14] Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes
Galzerano, Patrizia
Pesciaioli, Fabio
Mazzanti, Andrea
Bartoli, Giuseppe
Melchiorre, Paolo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (42) : 7892 - 7894
[15] Gilchrist T.L., 1996, Comprehensive Heterocyclic Chemistry II, V6, P279, DOI [DOI 10.1016/B978-008096518-5.00120-9, 10.1016/B978-008096518-5.00120-9]
[16] Grondal C, 2010, NAT CHEM, V2, P167, DOI [10.1038/NCHEM.539, 10.1038/nchem.539]
[17] Guo H.-C., 2006, Angew. Chem, V118, P362
[18] Catalytic asymmetric tandem transformations triggered by conjugate additions
Guo, HC
Ma, JA
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (03) : 354 - 366
[19] Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones
Hayashi, Y
Yamaguchi, J
Sumiya, T
Hibino, K
Shoji, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) : 5966 - 5973
[20] Direct proline-catalyzed asymmetric α-aminoxylation of ketones
Hayashi, Y
Yamaguchi, J
Sumiya, T
Shoji, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) : 1112 - 1115

← 1 2 3 4 5 6 7 8 →