Diastereoselectivity control of the radical carboazidation of substituted methylenecyclohexanes.

Cren S; Schär P; Renaud P; Schenk K

doi:10.1021/jo900088x

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Journal article

Diastereoselectivity control of the radical carboazidation of substituted methylenecyclohexanes.

Cren S Departement für Chemie and Biochemie, Universität Bern Freiestrasse 3, CH-3012 Bern, Switzerland.
Schär P
Renaud P
Schenk K

2009-03-27

Published in:

The Journal of organic chemistry. - 2009

English A systematic study of the diastereoselectivity of the radical carboazidation of methylenecyclohexane derivatives is presented. Several substitution patterns leading to a high level of stereocontrol have been identified. Axial attack is the preferred reaction pathway for cyclohexyl radicals, and excellent stereoselectivities can be obtained by introducing an axial substitutent at position 2. In this case, a second equatorial substituent at position 2 may be tolerated without a large detrimental effect on the diastereoselectivity. Finally, a high level of equatorial attack is observed with a very bulky substituent at position 2.

Language

English

Open access status

closed

Identifiers

DOI 10.1021/jo900088x
PMID 19320456

Persistent URL

https://sonar.ch/global/documents/1148

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