ENANTIODIFFERENTIATING TRANSFORMATION OF PROCHIRAL 1,3,5-PENTANETRIOLS CONTROLLED BY INTRAMOLECULAR VANDERWAALS ATTRACTIONS

被引：21

作者：

HARADA, T

WADA, I

UCHIMURA, JJ

INOUE, A

TANAKA, S

OKU, A

机构：

[1] Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)92049-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetalization of prochiral 1,3,5-pentanetriol derivatives (5) with l-menthone proceeded enantioselectively (3.0-4.6:1) to give chiral spiroacetals (6) which can be utilized as versatile chiral building blocks.

引用

页码：1219 / 1222

页数：4

共 16 条

[1] THE IMPORTANCE OF VANDERWAALS ATTRACTIONS IN DETERMINING THE EQUILIBRIUM BETWEEN 1,4-DIALKYLCYCLOOCTATETRAENES AND 1,6-DIALKYLCYCLOOCTATETRAENES [J].

ALLINGER, NL ;

FRIERSON, M ;

VANCATLEDGE, FA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4592-4593

[2] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[3] CRYSTAL AND MOLECULAR-STRUCTURE OF 2,4,6-TRIBROMO-1,3,5-TRINEOPENTYLBENZENE - INDICATIONS FOR ATTRACTIVE STERIC EFFECTS IN CRYSTAL [J].

AURIVILLIUS, B ;

CARTER, RE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (10) :1033-1037

[4] INTRAMOLECULAR VANDERWAALS ATTRACTION - CONFORMATIONAL-ANALYSIS OF DI(PRIMARY ALKYL) DERIVATIVES OF 5-MEMBERED AND 6-MEMBERED HETEROCYCLIC-SYSTEMS [J].

BERG, U ;

PETTERSSON, I .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5177-5184

[5] BARRIERS TO INTERNAL-ROTATION IN 1,3,5-TRINEOPENTYLBENZENES .8. MOLECULAR MECHANICS CALCULATIONS - THEORETICAL EVIDENCE FOR ATTRACTIVE STERIC EFFECTS [J].

CARTER, RE ;

STILBS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7515-7521

[6]

GABLER R, 1978, ELECTRICAL INTERACTI

[7] STEREOCHEMICAL CONTROL OF CONSECUTIVE STEREOGENIC CENTERS BY INTRAMOLECULAR HYDROBORATION OF DIALKENYL CARBINOL DERIVATIVES [J].

HARADA, T ;

MATSUDA, Y ;

WADA, I ;

UCHIMURA, J ;

OKU, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :21-22

[8] RESOLUTION OF 1,3-ALKANEDIOLS VIA CHIRAL SPIROKETALS DERIVED FROM L-MENTHONE [J].

HARADA, T ;

KUROKAWA, H ;

OKU, A .

TETRAHEDRON LETTERS, 1987, 28 (41) :4843-4846

[9] ENANTIODIFFERENTIATING FUNCTIONALIZATION OF MESO-1,3-DIOLS VIA SPIROACETALS DERIVED FROM L-MENTHONE [J].

HARADA, T ;

SAKAMOTO, K ;

IKEMURA, Y ;

OKU, A .

TETRAHEDRON LETTERS, 1988, 29 (25) :3097-3100

[10] STEREOSELECTIVE SYNTHESES OF BUILDING-BLOCKS WITH 3 CONSECUTIVE STEREOGENIC CENTERS - IMPORTANT PRECURSORS OF POLYKETIDE NATURAL-PRODUCTS [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (06) :489-503

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