Desymmetrization of unsaturated meso-1,2-diols via an intramolecular haloetherification of ene acetals:: A remarkable kinetic control

被引：16

作者：

Fujioka, H ^{[1
]}

Nagatomi, Y ^{[1
]}

Kotoku, N ^{[1
]}

Kitagawa, H ^{[1
]}

Kita, Y ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 40期

关键词：

asymmetric synthesis; diols; acetals; etherification;

D O I：

10.1016/S0040-4039(98)01566-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Haloetherification reaction of the chiral ene acetals derived from unsaturated meso-1,2-diols and chiral non-racemic norbornene aldehyde proceeded in an intramolecular manner with an unexpectedly high kinetic control. This method has been successfully employed for the desymmetrization of unsaturated meso-1,2-diols leading to their optically pure derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7309 / 7312

页数：4

共 23 条

[1] GLYCEROLATO-1O,2O COMPLEXES OF PLATINUM(II) - SOLID AND SOLUTION STATE STRUCTURES OF [(R-STAR,R-STAR),(R-STAR)]-(+/-)-[PTOCH2CH(O)CH2OH(1,2-C6H4(PMEPH)2)].2MEOH
APPELT, A
WILLIS, AC
WILD, SB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) : 938 - 940
[2] BANFI L, 1993, SYNTHESIS-STUTTGART, P1029
[3] Deracemization by enantiodifferentiating inversion in 1,3-diols
Davis, AP
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (06): : 591 - 594
[4] Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral alpha,alpha-disubstituted 1,3-propanediols
Fadel, A
Arzel, P
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (02) : 283 - 291
[5] Highly enantioselective asymmetrization of meso-1,2-diols through a novel and efficient reaction cycle
Fujioka, H
Nagatomi, Y
Kitagawa, H
Kita, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) : 12016 - 12017
[6] ENANTIODIFFERENTIATING FUNCTIONALIZATION OF CIS-CYCLOALKANE-1,2-DIOLS AND CIS-ENDO-5-NORBORNEN-2,3-YLENEBIS(METHANOL) VIA CHIRAL SPIROACETALS DERIVED FROM L-MENTHONE
HARADA, T
WADA, I
OKU, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2599 - 2605
[7] HARADA T, 1994, SYNLETT, P95
[8] AN ASYMMETRIC-SYNTHESIS OF GLYCEROL DERIVATIVES BY THE ENANTIOSELECTIVE ACYLATION OF PROCHIRAL GLYCEROL
ICHIKAWA, J
ASAMI, M
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1984, (06) : 949 - 952
[9] ISHIHARA K, 1994, SYNLETT, P611
[10] Desymmetrization of meso-1,2-diols via chiral Lewis acid-mediated ring-cleavage of 1,3-dioxolane derivatives
Kinugasa, M
Harada, T
Oku, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) : 9067 - 9068

← 1 2 3 →