A NOVEL ASYMMETRIC DESYMMETRISATION OF MESO-CYCLOPENTANE-1,2-DIOL VIA DIASTEREOSELECTIVE BETA-ELIMINATION OF CHIRAL ALPHA-ARYLSULFINYL ACETALS

被引：18

作者：

MAEZAKI, N ^{[1
]}

SOEJIMA, M ^{[1
]}

TAKEDA, M ^{[1
]}

SAKAMOTO, A ^{[1
]}

TANAKA, T ^{[1
]}

IWATA, C ^{[1
]}

机构：

[1] OSAKA UNIV, FAC PHARMACEUT SCI, SUITA, OSAKA 565, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 11期

关键词：

D O I：

10.1039/c39940001345

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

meso-Cyclopentane-1,2-diol was differentiated via diastereoselective C-O bond fission of the acetal utilising the anion stabilised by a neighbouring chiral sulfinyl group to provide the chiral alcohol.

引用

页码：1345 / 1346

页数：2

共 23 条

[1] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[2] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[3] ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF C11-C17 FRAGMENT OF TYLONOLIDE FROM ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE [J].

GUANTI, G ;

BANFI, L ;

GHIRON, C ;

NARISANO, E .

TETRAHEDRON LETTERS, 1991, 32 (02) :267-270

[4] ASYMMETRIC INDUCTION BY SULFINYL CHIRALITY - A TOTAL SYNTHESIS OF (+)-TALAROMYCIN A AND (-)-TALAROMYCIN-B [J].

IWATA, C ;

FUJITA, M ;

MORITANI, Y ;

HATTORI, K ;

IMANISHI, T .

TETRAHEDRON LETTERS, 1987, 28 (27) :3135-3138

[5] ASYMMETRIC FUNCTIONALIZATION OF PROCHIRAL 1,3-DIOLS BASED ON AN EFFICIENT 1,6-CHIRAL INDUCTION - THE DIASTEREOSELECTIVE C-O BOND FISSION IN CHIRAL BETA-ARYLSULFINYL ACETAL VIA 2 TYPES OF CHELATION CONTROL [J].

IWATA, C ;

MAEZAKI, N ;

MURAKAMI, M ;

SOEJIMA, M ;

TANAKA, T ;

IMANISHI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (06) :516-518

[6]

IWATA C, 1993, CHEM PHARM BULL, V41, P339

[7]

IWATA C, 1993, CHEM PHARM BULL, V41, P946

[8] ASYMMETRIC FUNCTIONALIZATION AT A PROCHIRAL CARBON CENTER BY THE AID OF SULFINYL CHIRALITY - A SELECTIVE FORMATION OF 6-SUBSTITUTED (3R,SS) AND (3S,SS)-3-HYDROXYMETHYL-3,4-DIHYDRO-5-(PARA-TOLYL)SULFINYL-2H-PYRANS [J].

IWATA, C ;

FUJITA, M ;

MORITANI, Y ;

SUGIYAMA, K ;

HATTORI, K ;

IMANISHI, T .

TETRAHEDRON LETTERS, 1987, 28 (27) :3131-3134

[9] ATTRACTIVE AND REPULSIVE GAUCHE EFFECTS [J].

JUARISTI, E .

JOURNAL OF CHEMICAL EDUCATION, 1979, 56 (07) :438-441

[10]

JUARISTI E, 1991, INTRO STEREOCHEMISTR, P271

← 1 2 3 →