Boron trifluoride-tetrahydrofuran complex: a superior trigger for the Yamaguchi-Hirao alkylation of lithio-acetylides by epoxides

被引：19

作者：

Evans, AB ^{[1
]}

Knight, DW ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 39期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(01)01414-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Use of (BF3THF)-T-. complex in place of the usual (BF3OEt2)-O-. analogue in the Yamaguchi-Hirao alkylation of lithio- acetylides 2 by monosubstituted epoxides 3 gives consistently superior isolated yields (ca. 90%) of homopropargylic alcohols 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6947 / 6948

页数：2

共 8 条

[1] Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols [J].

Bedford, SB ;

Bell, KE ;

Bennett, F ;

Hayes, CJ ;

Knight, DW ;

Shaw, DE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2143-2153

[2]

FRIED J, 1969, TETRAHEDRON LETT, P1379

[3]

FRIED J, 1968, J CHEM SOC CHEM COMM, P634

[4]

Garratt P.J., 1991, COMPREHENSIVE ORGANI, V3, P271

[5] A stereochemically flexible approach to pyrrolidines based on 5-endo-trig iodocyclisations of homoallylic sulfonamides [J].

Jones, AD ;

Knight, DW ;

Hibbs, DE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (10) :1182-1203

[6] Remarkable catalytic activity of Me3Ga in the alkylation of hetero-substituted epoxides with alkynyllithiums [J].

Ooi, T ;

Morikawa, J ;

Ichikawa, H ;

Maruoka, K .

TETRAHEDRON LETTERS, 1999, 40 (32) :5881-5884

[7] THE CATALYTIC ACTION OF TRIMETHYLGALLIUM ON THE REACTION OF ALKYNYLLITHIUM WITH EPOXIDES [J].

UTIMOTO, K ;

LAMBERT, C ;

FUKUDA, Y ;

SHIRAGAMI, H ;

NOZAKI, H .

TETRAHEDRON LETTERS, 1984, 25 (47) :5423-5426

[8] AN EFFICIENT METHOD FOR THE ALKYNYLATION OF OXIRANES USING ALKYNYL BORANES [J].

YAMAGUCHI, M ;

HIRAO, I .

TETRAHEDRON LETTERS, 1983, 24 (04) :391-394

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