Stereoselectivity in Reactions of 1,2‐Dioxy‐Substituted Radicals under Chelation Control: An Unexpected Result | Zendy

Gerster Michèle | Zendy; Schenk Kurt | Zendy; Renaud Philippe | Zendy

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Stereoselectivity in Reactions of 1,2‐Dioxy‐Substituted Radicals under Chelation Control: An Unexpected Result

Author(s) -

Gerster Michèle,

Schenk Kurt,

Renaud Philippe

Publication year - 1996

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199623961

Subject(s) - chelation , radical , diastereomer , substituent , stereoselectivity , chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis

The strong pyramidalization of the radical intermediates (shown on the right) is the reason why anti Cram chelation products are obtained in the reduction of 1,2‐dialkyl‐1,2‐dioxy‐substituted radicals, even though a chelate is formed. The main diastereoisomer results from an attack syn to the large substituent R 2 . R 1 CH 2 CHCHCH 2 SnBu 3 , R 2 t Bu, R para ‐methoxyphenyl.

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