A new norephedrine-derived chiral base for epoxide rearrangement reactions

被引：41

作者：

de Sousa, SE ^{[1
]}

O'Brien, P ^{[1
]}

Steffens, HC ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 48期

关键词：

diamines; epoxides; rearrangement; allylic alcohols;

D O I：

10.1016/S0040-4039(99)01740-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion of (1R,2S)-norephedrine into a novel chiral diamine (83% yield, simple two step synthesis) and its use as a chiral base in two epoxide rearrangement reactions is reported. Rearrangement of a 4,5-disubstituted cyclohexene oxide and of a 4-aminosubstituted cyclopentene oxide generated allylic alcohols of >90% ee. These results represent the highest levels of enantioselectivity reported to date for such substrates. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8423 / 8425

页数：3

共 13 条

[1] A novel highly effective chiral lithium amide for catalytic enantioselective deprotonation of meso-epoxides
Asami, M
Suga, T
Honda, K
Inoue, S
[J]. TETRAHEDRON LETTERS, 1997, 38 (36) : 6425 - 6428
[2] An asymmetric synthesis of (1S,4R)-4-amino-2-cyclopentenol derivatives
Asami, M
Ogawa, M
Inoue, S
[J]. TETRAHEDRON LETTERS, 1999, 40 (08) : 1563 - 1564
[3] Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides
Bhuniya, D
DattaGupta, A
Singh, VK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) : 6108 - 6113
[4] Two expedient methods for the preparation of chiral diamines
de Sousa, SE
O'Brien, P
Poumellec, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09): : 1483 - 1492
[5] Two useful methods for the preparation of (R)- and (S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)ethanamine
deSousa, SE
OBrien, P
Poumellec, P
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2613 - 2618
[6] STEREOSELECTIVE AND REGIOSELECTIVE SYNTHESIS OF CHIRAL DIAMINES AND TRIAMINES FROM PSEUDOEPHEDRINE AND EPHEDRINE
DIETER, RK
DEO, N
LAGU, B
DIETER, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) : 1663 - 1671
[7] Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
O'Brien, P
Towers, TD
Voith, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (44) : 8175 - 8178
[8] Chiral lithium amide base-mediated rearrangement of bis-protected meso-4,5-dihydroxy cyclohexene oxides:: enantioselective synthesis of (4R,5S)- and (4S,5R)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone
O'Brien, P
Poumellec, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15): : 2435 - 2441
[9] Recent advances in asymmetric synthesis using chiral lithium amide bases
O'Brien, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (08): : 1439 - 1457
[10] OBRIEN P, 1999, TETRAHEDRON LETT, V40

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