Highly Diastereo- and Enantioselective Intramolecular Amidation of Saturated CH Bonds Catalyzed by Ruthenium Porphyrins

Virtually complete diastereoselectivity is observed in the intramolecular amidation of saturated CH bonds, catalyzed by the ruthenium porphyrin catalyst 1 or 2. Reactions of sulfamate esters with PhI(OAc)2 in the presence of 1 or 2 afforded cyclic sulfamidates in up to 87 % ee.

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 41; no. 18; pp. 3465 - 3468
Main Authors Liang, Jiang-Lin, Yuan, Shi-Xue, Huang, Jie-Sheng, Yu, Wing-Yiu, Che, Chi-Ming
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.09.2002
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
Chemistry
Chemistry, Multidisciplinary
cyclization
Physical Sciences
porphyrinoids
ruthenium
Science & Technology
sulfamidates
HYDROCARBONS
NITROGEN-ATOM-TRANSFER
CRYSTAL-STRUCTURE
CYCLOPROPANATION
CHIRAL RUTHENIUM
asymmetric catalysis
sulfamidates
cyclization
porphyrinoids
ruthenium
ALKENES
MANGANESE-PORPHYRINS
AZIRIDINATION
ASYMMETRIC EPOXIDATION
ALKANES
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Summary:Virtually complete diastereoselectivity is observed in the intramolecular amidation of saturated CH bonds, catalyzed by the ruthenium porphyrin catalyst 1 or 2. Reactions of sulfamate esters with PhI(OAc)2 in the presence of 1 or 2 afforded cyclic sulfamidates in up to 87 % ee.
Bibliography:ark:/67375/WNG-1J75QWBS-N
ArticleID:ANIE3465
This work was supported by The University of Hong Kong, the Hong Kong Research Grants Council, the Hong Kong University Foundation, and the University Grants Committee of the Hong Kong SAR of China (Area of Excellence Scheme, AoE/P-10/01). We thank Dr. Nianyong Zhu for assistance in solving the crystal structures reported herein.
istex:CB40D7A262C92C21A021AFAFA534C022259E8294
This work was supported by The University of Hong Kong, the Hong Kong Research Grants Council, the Hong Kong University Foundation, and the University Grants Committee of the Hong Kong SAR of China (Area of Excellence Scheme, AoE/P‐10/01). We thank Dr. Nianyong Zhu for assistance in solving the crystal structures reported herein.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020916)41:18<3465::AID-ANIE3465>3.0.CO;2-D