INTRAMOLECULAR METALLO-ENE-ALLENE REACTIONS - A NEW CARBOCYCLES SYNTHESIS

被引：51

作者：

MEYER, C ^{[1
]}

MAREK, I ^{[1
]}

COURTEMANCHE, G ^{[1
]}

NORMANT, JF ^{[1
]}

机构：

[1] UNIV PARIS 06,CHIM ORGANOELEMENTS LAB,F-75252 PARIS 05,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 04期

关键词：

D O I：

10.1021/jo00109a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polysubstituted enynes have been lithiated on the propargylic position, and transmetalation to the corresponding zinc reagents promotes an easy cyclization reaction leading to polysubstituted cyclopentylmethylzinc derivatives. This cyclization is stereospecific, and a single diastereoisomer is formed, even when a tertiary and a quaternary center are linked in the process. The reaction is considered to take place via a metallo-ene-allene process.

引用

页码：863 / 871

页数：9

共 57 条

[1]

[Anonymous], 1981, SYNTHESIS ACETYLENES

[2] SINGLE ELECTRON-TRANSFER IN METAL HALOGEN EXCHANGE - THE REACTION OF ORGANOLITHIUM COMPOUNDS WITH ALKYL-HALIDES [J].

ASHBY, EC ;

PHAM, TN .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1291-1300

[3] STEREOSELECTIVITY OF CYCLIZATION OF SUBSTITUTED 5-HEXEN-1-YLLITHIUMS - REGIOSPECIFIC AND HIGHLY STEREOSELECTIVE INSERTION OF AN UNACTIVATED ALKENE INTO A C-LI BOND [J].

BAILEY, WF ;

KHANOLKAR, AD ;

GAVASKAR, K ;

OVASKA, TV ;

ROSSI, K ;

THIEL, Y ;

WIBERG, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5720-5727

[4] HIGHLY STEREOSELECTIVE TANDEM CYCLIZATIONS OF 5-HEXENYLLITHIUMS - PREPARATION OF ENDO-2-SUBSTITUTED BICYCLO[2.2.1]HEPTANES AND 3-SUBSTITUTED TRANS-BICYCLO[3.3.0]OCTANES [J].

BAILEY, WF ;

KHANOLKAR, AD ;

GAVASKAR, KV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8053-8060

[5] THE CONVERSION OF 4-OXA-5-HEXENYLLITHIUMS TO 4-ALKEN-1-OLS - A NOVEL [1,4]-WITTIG REARRANGEMENT [J].

BAILEY, WF ;

ZARCONE, LMJ .

TETRAHEDRON LETTERS, 1991, 32 (35) :4425-4426

[6] ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS [J].

BAJGROWICZ, JA ;

ELHALLAOUI, A ;

JACQUIER, R ;

PIGIERE, C ;

VIALLEFONT, P .

TETRAHEDRON, 1985, 41 (10) :1833-1843

[7]

BATTIONI JP, 1969, B CHIM FR, V3, P981

[8]

BATTIONI JP, 1969, B CHIM FR, V3, P976

[9]

BERNADOU F, 1976, TETRAHEDRON LETT, P3083

[10] CONFORMATIONAL FREE-ENERGY DIFFERENCE (-DELTA-GDEGREES VALUE) OF METHYL-GROUP IN METHYLCYCLOHEXANE - ACCURATE DETERMINATION BY DIRECT, LOW-TEMPERATURE NUCLEAR MAGNETIC-RESONANCE METHOD [J].

BOOTH, H ;

EVERETT, JR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (08) :278-279

← 1 2 3 4 5 6 →