A route to 1,2-diols by enantioselective organocatalytic α-oxidation with molecular oxygen

被引：58

作者：

Ibrahem, Ismail ^{[1
]}

Zhao, Gui-Ling ^{[1
]}

Sunden, Henrik ^{[1
]}

Cordova, Armando ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 27期

基金：

瑞典研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2006.04.133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route to 1,2-diols by the direct organocatalytic enantioselective alpha-oxidation of aldehydes using molecular oxygen is presented. Protected commercially available chiral pyrrolidines catalyze the asymmetric alpha-oxidation of aldehydes with singlet molecular oxygen with high enantioselectivity to furnish the corresponding diols after in situ reduction in high yield with up to 98% ee. Electrophilic singlet molecular oxygen was photo or chemically generated ('dark' O-1(2)). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4659 / 4663

页数：5

共 45 条

[21] Enders D, 1996, LIEBIGS ANN, P11
[22] PHOTOSENSITIZED OXYGENATIONS AND ROLE OF SINGLET OXYGEN
FOOTE, CS
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1968, 1 (04) : 104 - &
[23] A general organocatalyst for direct α-functionalization of aldehydes:: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions.: Scope and mechanistic insights
Franzén, J
Marigo, M
Fielenbach, D
Wabnitz, TC
Kjaersgaard, A
Jorgensen, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 18296 - 18304
[24] Hanessian S., 1983, TOTAL SYNTHESIS NATU
[25] 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
[26] 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
[27] Direct proline catalyzed asymmetric α-aminooxylation of aldehydes
Hayashi, Y
Yamaguchi, J
Hibino, K
Shoji, M
[J]. TETRAHEDRON LETTERS, 2003, 44 (45) : 8293 - 8296
[28] DIASTEREOSELECTIVE NUCLEOPHILIC ADDITIONS ON A CHIRAL GLYOXAL MONOACETAL
HEITZ, MP
GELLIBERT, F
MIOSKOWSKI, C
[J]. TETRAHEDRON LETTERS, 1986, 27 (33) : 3859 - 3860
[29] Recent advances in catalytic, enantioselective α aminations and α oxygenations of carbonyl compounds
Janey, JM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) : 4292 - 4300
[30] CATALYTIC ASYMMETRIC DIHYDROXYLATION
KOLB, HC
VANNIEUWENHZE, MS
SHARPLESS, KB
[J]. CHEMICAL REVIEWS, 1994, 94 (08) : 2483 - 2547

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