Desymmetrization of meso-1,3-tetrols via oxazaborolidine-mediated enantiotopic group selective ring-cleavage of bisacetal derivatives

被引：10

作者：

Harada, T ^{[1
]}

Egusa, T ^{[1
]}

Oku, A ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem, Sakyo Ku, Kyoto 606, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

acetals; asymmetric induction; cleavage reactions; polyols;

D O I：

10.1016/S0040-4039(98)01092-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Meso-1,3,5,7-heptanetetrol and -1,3,6,8-octanetetrol were desymmetrized via enantiotopic group selective ring-cleavage reaction of their bisacetal derivatives using a chiral oxazaborolidine. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5535 / 5536

页数：2

共 8 条

[1] A NOVEL METHOD FOR THE INSITU GENERATION OF ALKOXYDIALKYLBORANES AND THEIR USE IN THE SELECTIVE PREPARATION OF 1,3-SYN DIOLS [J].

CHEN, KM ;

GUNDERSON, KG ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

CHEMISTRY LETTERS, 1987, (10) :1923-1926

[2] A HIGHLY CONVERGENT ASYMMETRIC-SYNTHESIS OF THE C(19)-C(27) SEGMENT OF RIFAMYCIN-S - AN APPLICATION OF ENANTIODIFFERENTIATING ACETALIZATION WITH MENTHONE [J].

HARADA, T ;

KAGAMIHARA, Y ;

TANAKA, S ;

SAKAMOTO, K ;

OKU, A .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1637-1639

[3] Kinetic resolution of cyclic acetals derived from 1,3-alkanediols via oxazaborolidine-mediated enantioselective ring-cleavage reaction [J].

Harada, T ;

Egusa, T ;

Kinugasa, M ;

Oku, A .

TETRAHEDRON LETTERS, 1998, 39 (31) :5531-5534

[4] 2-DIRECTIONAL SYNTHESIS AND ITS USE IN NATURAL PRODUCT SYNTHESIS [J].

MAGNUSON, SR .

TETRAHEDRON, 1995, 51 (08) :2167-2213

[5] NOVEL-APPROACH TO REMOTE ASYMMETRIC INDUCTION IN CARBONYL ADDITION AND RELATED REACTIONS [J].

MOLANDER, GA ;

HAAR, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :40-49

[6] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[7]

SCHREIBER SL, 1987, CHEM SCRIPTA, V27, P563

[8] REACTIONS THAT PROCEED WITH A COMBINATION OF ENANTIOTOPIC GROUP AND DIASTEREOTOPIC FACE SELECTIVITY CAN DELIVER PRODUCTS WITH VERY HIGH ENANTIOMERIC EXCESS - EXPERIMENTAL SUPPORT OF A MATHEMATICAL-MODEL [J].

SCHREIBER, SL ;

SCHREIBER, TS ;

SMITH, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1525-1529

← 1 →