New protocol for allylic substitution with aryl and alkenyl copper reagents derived from organolithiums

被引：15

作者：

Kiyotsuka, Yohei ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 51期

关键词：

D O I：

10.1016/j.tetlet.2008.10.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substitution of allylic picolinoates with copper reagents derived from sp(2)-carbon-lithiums and CuBr center dot Me2S was established to furnish anti S(N)2' products with almost perfect regioselectivity and chirality transfer. The preparations of organolithiums such as lithium-halogen exchange and ortho lithiation were coupled to the substitution to install various sp(2)-carbon groups, which include Ph, 2,6-Me2C6H3, 4-Me-2,6(MOMO)C6H2, and cis and trans 1-heptenyl groups. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：7256 / 7259

页数：4

共 37 条

[1] Diastereoselective reactions of δ-oxy-substituted allylic acetates with organocopper reagents [J].

Belelie, JL ;

Chong, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3000-3006

[2] Stereoselective reactions of acyclic allylic phosphates with organocopper reagents [J].

Belelie, JL ;

Chong, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5552-5555

[3]

Borthwick S., 2006, TETRAHEDRON LETT, V47, P7205

[4] Stereospecific and stereodivergent construction of quaternary carbon centers through switchable directed/nondirected allylic substitution [J].

Breit, B ;

Demel, P ;

Studte, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3786-3789

[5] Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution [J].

Breit, B ;

Herber, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3790-3792

[6]

Breit B, 2001, ADV SYNTH CATAL, V343, P429, DOI 10.1002/1615-4169(200107)343:5<429::AID-ADSC429>3.3.CO

[7]

2-B

[8] O-DPPB-Directed copper-mediated allylic substitution: Part 3. Stereospecific and stereodivergent construction of tertiary and quaternary carbon centers through switchable directed/nondirected allylic substitution [J].

Breit, Bernhard ;

Demel, Peter ;

Grauer, Daniel ;

Studte, Christopher .

CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (04) :586-597

[9] Iron-catalyzed alkylation of alkenyl Grignard reagents [J].

Cahiez, Gerard ;

Duplais, Christophe ;

Moyeux, Alban .

ORGANIC LETTERS, 2007, 9 (17) :3253-3254

[10] Stereoselective SN2-substitutions using polyfunctional lithium arylcuprates prepared by an exchange iodine-copper [J].

Calaza, MI ;

Yang, XY ;

Soorukram, D ;

Knochel, P .

ORGANIC LETTERS, 2004, 6 (04) :529-531

← 1 2 3 4 →