The cycloaddition of nitrones with homochiral cyclopropanes

被引：99

作者：

Sapeta, Katarina ^{[1
]}

Kerr, Michael A. ^{[1
]}

机构：

[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 22期

关键词：

D O I：

10.1021/jo701606u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloaddition of nitrones and enantiomerically pure cyclopropane-1,1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitution. Optically active 2-substituted cyclopropane-1,1-dicarboxylates are shown to racemize under typical reaction conditions, providing evidence for a zwitterionic ring-opened intermediate.

引用

页码：8597 / 8599

页数：3

共 17 条

[1] Total synthesis of (+)-phyllantidine [J].

Carson, Cheryl A. ;

Kerr, Michael A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6560-6563

[2] Magnesium iodide promoted reactions of nitrones with cyclopropanes: A synthesis of tetrahydro-1,2-oxazines [J].

Ganton, MD ;

Kerr, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8554-8557

[3]

Gothelf KV, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P211

[4] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

[5] Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2000, (16) :1449-1458

[6]

Kanemasa S, 2002, SYNLETT, P1371

[7] Highly enantioselective and diastereoselective cycloaddition of cyclopropanes with nitrones and its application in the kinetic resolution of 2-substituted cyclopropane-1,1-dicarboxylates [J].

Kang, Yan-Biao ;

Sun, Xiu-Li ;

Tang, Yong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3918-3921

[8]

Padwa A., 1984, DIPOLAR CYCLOADDITIO, V1

[9]

Pulz R, 2000, SYNLETT, P983

[10] Enantioselective addition of nitrones to activated cyclopropanes [J].

Sibi, MP ;

Ma, ZH ;

Jasperse, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5764-5765

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