Regio- and Stereocontrol Elements in Rh(II)-Catalyzed Intramolecular C−H Insertion of α-Diazo-α-(phenylsulfonyl)acetamides

Intramolecular C−H insertion reaction of α-diazo-α-(phenylsulfonyl)acetamides proceeded with high regio- and stereoselectivities to afford highly functionalized γ-lactams predominantly or exclusively. The high regioselectivity was attributed to the use of the phenylsulfonyl moiety, which altered ele...

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Bibliographic Details
Published in:Organic letters 2001-11, Vol.3 (22), p.3539-3542
Main Authors: Yoon, Cheol Hwan, Zaworotko, Michael J, Moulton, Brian, Jung, Kyung Woon
Format: Article
Language:English
Subjects:
Acetamides - chemical synthesis
Azo Compounds - chemical synthesis
Catalysis
Indicators and Reagents
Models, Molecular
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
Rhodium
Stereoisomerism
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Summary:Intramolecular C−H insertion reaction of α-diazo-α-(phenylsulfonyl)acetamides proceeded with high regio- and stereoselectivities to afford highly functionalized γ-lactams predominantly or exclusively. The high regioselectivity was attributed to the use of the phenylsulfonyl moiety, which altered electron density at the carbenoid center and exerted a steric effect during the insertion reaction. Also described herein are three control elements to determine regioselectivity, which are amide conformational, stereoelectronic, and substituent effects.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016647l