A triple umpolung sequence for the preparation of highly substituted indanes.

被引：7

作者：

Harrowven, DC ^{[1
]}

Browne, R ^{[1
]}

机构：

[1] UNIV NOTTINGHAM,NOTTINGHAM NG7 2RD,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 47期

关键词：

D O I：

10.1016/0040-4020(96)00907-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The paper describes a new method for the diastereoselective construction of highly substituted indanes. The key step involves a triple umpolung sequence in which a 2-lithio-2-vinyl-1,3-dithiane is first united with an aryl halide to form a ketenedithioacetal. Transmetallation of the aryl halide with an alkyllithium reagent then generates an alkyl halide and a 2-indanyl-2-lithio-1,3-dithiane. Finally, these combine to complete the sequence. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：14951 / 14960

页数：10

共 32 条

[1]

ANDERSEN NH, 1978, TETRAHEDRON LETT, P4315

[2]

Bellingham R, 1996, SYNTHESIS-STUTTGART, P285

[3]

COOK MJ, 1984, COMPREHENSIVE HETERO, V3, P943

[4] METHOD FOR PROTECTION OF LACTONES AND ESTERS AGAINST NUCLEOPHILIC ATTACK [J].

COREY, EJ ;

BEAMES, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) :5829-5831

[5]

GROBEL BT, 1977, SYNTHESIS-STUTTGART, P357

[6] DICHOTOMY IN THE ADDITION OF CARBON-CENTERED RADICALS TO KETENEDITHIOACETALS [J].

HARROWVEN, DC ;

BROWNE, R .

TETRAHEDRON LETTERS, 1994, 35 (29) :5301-5302

[7] MICHAEL INITIATED RING-CLOSURE REACTIONS IN NATURAL PRODUCT SYNTHESIS - A CONCISE ENTRY TO THE PODOPHYLLINS [J].

HARROWVEN, DC .

TETRAHEDRON, 1993, 49 (40) :9039-9048

[8] AN INSIGHT INTO THE T-BUTYLBROMIDE DIMETHYL-SULFOXIDE REAGENT - A NOVEL APPLICATION IN LIGNAN TOTAL SYNTHESIS [J].

HARROWVEN, DC ;

DENNISON, ST .

TETRAHEDRON LETTERS, 1993, 34 (20) :3323-3326

[9] A CONCISE SYNTHESIS OF TAIWANIN-E USING A MICHAEL INITIATED RING-CLOSURE PROTOCOL [J].

HARROWVEN, DC .

TETRAHEDRON LETTERS, 1991, 32 (30) :3735-3738

[10] CASCADE RADICAL REACTIONS IN SYNTHESIS - CONDENSED THIOPHENES FROM KETENETHIOACETALS [J].

HARROWVEN, DC .

TETRAHEDRON LETTERS, 1993, 34 (35) :5653-5656

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