Asymmetric desymmetrization of 2-substituted 1,3-propanediols by using oxazaborolidinone-mediated enantioselective ring-cleavage of prochiral acetal derivatives

被引：0

作者：

Harada, T ^{[1
]}

Imai, K ^{[1
]}

Oku, A ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

SYNLETT | 2002年 / 06期

关键词：

asymmetric synthesis; acetals; cleavage; diols; Lewis acids;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nonenzymatic desymmetrization of 2-substituted 1,3-propanediols leading to the enantiomerically enriched 3-benzyloxy-1-propanols was achieved by using oxazaborolidinone-mediated enantioselective ring-cleavage reaction of the dioxane acetal derivatives.

引用

页码：972 / 974

页数：3

共 12 条

[1] Asymmetric desymmetrization of 2-substituted 1,3-propanediols via catalytic enantioselective ring-cleavage reaction of cyclic acetal derivatives
Harada, T
Shiraishi, K
SYNLETT, 2005, (13) : 1999 - 2002
[2] Chiral oxazaborolidinone-mediated enantioselective ring-cleavage reaction of a mixture of diastereomeric 1,3-dioxolane acetals:: Application to asymmetric desymmetrization of meso-1,2-diols
Harada, T
Yamanaka, H
Oku, A
SYNLETT, 2001, (01) : 61 - 64
[3] Inter- and intramolecular differentiation of enantiotopic dioxane acetals through oxazaborolidinone-mediated enantioselective ring-cleavage reaction:: Kinetic resolution of racemic 1,3-alkanediols and asymmetric desymmetrization of meso-1,3-polyols
Harada, T
Egusa, T
Igarashi, Y
Kinugasa, M
Oku, A
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7080 - 7090
[4] Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate
Akai, S
Naka, T
Takebe, Y
Kita, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (10) : 1519 - 1523
[5] Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral alpha,alpha-disubstituted 1,3-propanediols
Fadel, A
Arzel, P
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) : 283 - 291
[6] Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate
Akai, S
Naka, T
Fujita, T
Takeba, Y
Tsujino, T
Kita, Y
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02): : 411 - 419
[7] Comparison of the chiral recognition of prochiral substrates in the acetylation reaction by a novel lipase (CSL) from the yeast, Cryptococcus spp. S-2 with immobilized PPL enzyme-catalyzed desymmetrization and asymmetrization of prochiral 2-substituted 1,3-propanediols by CSL and immobilized PPL
Lin, C
Hiraga, Y
Masaki, K
Iefuji, H
Ohkata, K
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2006, 38 (01) : 1 - 10
[8] Desymmetrization of meso-1,2-diols via chiral Lewis acid-mediated ring-cleavage of 1,3-dioxolane derivatives
Kinugasa, M
Harada, T
Oku, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) : 9067 - 9068
[9] Enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-propanediamines via asymmetric para-aminations of anilines
Zhang, Dekun
Chen, Yunrong
Lai, Yongning
Yang, Xiaoyu
CELL REPORTS PHYSICAL SCIENCE, 2021, 2 (05):
[10] ENANTIOSELECTIVE FUNCTIONALIZATION OF PROCHIRAL DIOLS VIA CHIRAL SPIROKETALS - PREPARATION OF OPTICALLY PURE 2-SUBSTITUTED 1,3-PROPANEDIOL DERIVATIVES AND ASYMMETRIC-SYNTHESIS OF CHROMAN RING AND SIDE-CHAIN OF ALPHA-TOCOPHEROL
HARADA, T
HAYASHIYA, T
WADA, I
IWAAKE, N
OKU, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) : 527 - 532

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