Stereoselective Simmons-Smith Cyclopropanation of Chiral Enamides

Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to >95:5). The application of this methodology to the synthesis of biologically significant aminoc...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 46; no. 22; pp. 4069 - 4072
Main Authors Song, Zhenlei, Lu, Ting, Hsung, Richard P., Al-Rashid, Ziyad F., Ko, Changhong, Tang, Yu
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 25.05.2007
WILEY‐VCH Verlag
Wiley
Subjects
aminocyclopropanes
Chemistry
Chemistry, Multidisciplinary
chiral enamides
conformation analysis
cyclopropanation
diastereoselectivity
Physical Sciences
Science & Technology
conformation analysis
ASYMMETRIC-SYNTHESIS
ALKYNYL BROMIDES
LOBATAMIDE-C
KEY COMPONENT
ALPHA-AMINO-ACIDS
BOND FORMATION
diastereoselectivity
cyclopropanation
aminocyclopropanes
QUINOLONECARBOXYLIC ACID
NEW-GENERATION
VINYL HALIDES
STEREOCHEMICAL ASSIGNMENT
chiral enamides
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Summary:Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to >95:5). The application of this methodology to the synthesis of biologically significant aminocyclopropanes illustrates the potential of chiral enamides as useful building blocks for stereoselective organic synthesis.
Bibliography:We thank NIH-NIGMS (GM066055) and UW-Madison for financial support. We also thank Ben Kucera and Vic Young for solving the X-ray crystal structures.
istex:24E864086F46C09AB8654C7BC034E3501AC79C73
NIH-NIGMS - No. GM066055
ark:/67375/WNG-4SKN852D-5
UW-Madison
ArticleID:ANIE200700681
We thank NIH‐NIGMS (GM066055) and UW‐Madison for financial support. We also thank Ben Kucera and Vic Young for solving the X‐ray crystal structures.
Medline
NIH RePORTER
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200700681