DIASTEREOSELECTIVE SYNTHESIS OF TRANS-1,2-DISUBSTITUTED CYCLOPROPANOLS FROM HOMOALLYL OR BIS-HOMOALLYL ESTERS VIA TANDEM INTRAMOLECULAR NUCLEOPHILIC ACYL SUBSTITUTION AND INTRAMOLECULAR CARBONYL ADDITION-REACTIONS MEDIATED BY TI(OPR-I)(4)/2 I-PRMGBR REAGENT

被引:91
作者
KASATKIN, A [1 ]
SATO, F [1 ]
机构
[1] TOKYO INST TECHNOL,DEPT BIOMOLEC ENGN,MIDORI KU,YOKOHAMA 226,KANAGAWA,JAPAN
关键词
D O I
10.1016/0040-4039(95)01208-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of homoallyl or bis-homoallyl esters with Ti(OPr-i)(4)/ 2 i-PrMgBr reagent resulted in intramolecular nucleophilic acyl substitution reaction and successive intramolecular carbonyl addition reaction providing trans-1,2-disubstituted cyclopropanols stereoselectively in excellent yields.
引用
收藏
页码:6079 / 6082
页数:4
相关论文
共 16 条
[1]   METAL-COMPLEXES OF SMALL CYCLOALKYNES AND ARYNES [J].
BENNETT, MA ;
SCHWEMLEIN, HP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (10) :1296-1320
[2]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[3]   SYNTHESIS AND REACTIVITY OF A TITANOCENE BENZYNE COMPLEX [J].
CAMPORA, J ;
BUCHWALD, SL .
ORGANOMETALLICS, 1993, 12 (10) :4182-4187
[4]  
Caputo R, 1991, COMPREHENSIVE ORGANI, P139
[5]   CATALYTIC DIASTEREOSELECTIVE SYNTHESIS OF CIS-1,2-DISUBSTITUTED CYCLOPROPANOLS FROM ESTERS USING A VICINAL DICARBANION EQUIVALENT [J].
COREY, EJ ;
RAO, SA ;
NOE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9345-9346
[6]   GENERATION AND REACTIONS OF LOW-VALENT TITANIUM ALKOXIDE-ACETYLENE COMPLEXES - A PRACTICAL PREPARATION OF ALLYL ALCOHOLS [J].
HARADA, K ;
URABE, H ;
SATO, F .
TETRAHEDRON LETTERS, 1995, 36 (18) :3203-3206
[7]   NEW, EFFICIENT METHOD FOR THE SYNTHESIS OF ALLYLTITANIUM COMPOUNDS FROM ALLYL HALIDES OR ALLYL ALCOHOL DERIVATIVES VIA OXIDATIVE ADDITION - A HIGHLY EFFICIENT AND PRACTICAL SYNTHESIS OF HOMOALLYL ALCOHOLS [J].
KASATKIN, A ;
NAKAGAWA, T ;
OKAMOTO, S ;
SATO, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (13) :3881-3882
[8]  
KASATKIN A, UNPUB TETRAHEDRON LE
[9]  
KULINKOVICH OG, 1989, ZH ORG KHIM+, V25, P2244
[10]   TITANIUM(IV) ISOPROPOXIDE-CATALYZED FORMATION OF 1-SUBSTITUTED CYCLOPROPANOLS IN THE REACTION OF ETHYLMAGNESIUM BROMIDE WITH METHYL ALKANECARBOXYLATES [J].
KULINKOVICH, OG ;
SVIRIDOV, SV ;
VASILEVSKI, DA .
SYNTHESIS-STUTTGART, 1991, (03) :234-234