α-Sulfinyl carbanions as a new source of olefins

被引：24

作者：

Abramovitch, A ^{[1
]}

Varghese, JP

Marek, I

机构：

[1] Technion Israel Inst Technol, Dept Chem, IL-32000 Haifa, Israel

[2] Technion Israel Inst Technol, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 04期

关键词：

D O I：

10.1021/ol036450o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Secondary alpha-lithiosulfinyl carbanions react either intermolecularly, after transmetalation into an organocopper derivative in an S(N)2-type process with zinc carbenoid, or intramolecularly via higher-order zincate to give, through a tandem zinc homologation-beta-elimination reaction the corresponding alkenes. alpha,alpha-Disubstituted alkenes are only formed from tertiary alpha-lithiosulfinyl carbanions via the 1,2-metalate rearrangement.

引用

页码：621 / 623

页数：3

共 43 条

[1] Lithiated beta-aminoalkyl sulfones as mono and dinucleophiles in the preparation of nitrogen heterocycles: Application to the synthesis of capsazepine [J].

Alonso, DA ;

Costa, A ;

Mancheno, B ;

Najera, C .

TETRAHEDRON, 1997, 53 (13) :4791-4814

[2] Lithiated gamma-tosyl-substituted benzylmethallylamine: New gamma-amino methallyl sulfone anions in organic synthesis [J].

Alonso, DA ;

Falvello, LR ;

Mancheno, B ;

Najera, C ;

Tomas, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5004-5012

[3] alpha-nitrogenated organolithium compounds from alpha-amidomethyl and alpha-aminomethyl sulfones [J].

Alonso, DA ;

Alonso, E ;

Najera, C ;

Ramon, DJ ;

Yus, M .

TETRAHEDRON, 1997, 53 (13) :4835-4856

[4] A new approach towards the synthesis of sp3 1,1-diiodoalkanes [J].

Aufauvre, L ;

Knochel, P ;

Marek, I .

CHEMICAL COMMUNICATIONS, 1999, (21) :2207-2208

[5] THE COPPER(I)-CATALYZED COUPLING OF GRIGNARD-REAGENTS WITH 5-LITHIO-2,3-DIHYDROFURAN AND 6-LITHIO-3,4-DIHYDRO-2H-PYRAN [J].

BARBER, C ;

BURY, P ;

KOCIENSKI, P ;

OSHEA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) :1595-1597

[6] Preparation, solid-state structure, and synthetic applications of isolable and storable haloalkylzinc reagents [J].

Charette, AB ;

Marcoux, JF ;

Molinaro, C ;

Beauchemin, A ;

Brochu, C ;

Isabel, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4508-4509

[7] Diastereo- and enantioselective synthesis of 1,2,3-substituted cyclopropanes with zinc carbenoids [J].

Charette, AB ;

Lemay, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (10) :1090-1092

[8] A CONVENIENT PREPARATION OF MONO-DI-HALOGENOALKENES OR GEM-DI-HALOGENOALKENES FROM ALPHA-SULFONYL CARBANIONS AND HALOGENOLITHIOCARBENOIDS [J].

CHARREAU, P ;

JULIA, M ;

VERPEAUX, JN .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 379 (03) :201-210

[9]

CHEMLA F, 1993, SYNLETT, P665

[10] TOTAL SYNTHESIS OF MAYTANSINE [J].

COREY, EJ ;

WEIGEL, LO ;

CHAMBERLIN, AR ;

CHO, H ;

HUA, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6613-6615

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