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On the Unexpected Stereochemical Outcome of the Magnesium in Methanol – Conjugate Reduction of an Exocyclic α,β‐Unsaturated Ester
Author(s) -
Gabriëls Stefan,
Van Haver Dirk,
Vandewalle Maurits,
De Clercq Pierre,
Viterbo Davide
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199908)1999:8<1803::aid-ejoc1803>3.0.co;2-l
Subject(s) - chemistry , conjugate , diastereomer , magnesium , methanol , stereochemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics
The conjugate reduction of the exo cyclic α,β‐unsaturated ester 9 with magnesium in methanol gives a mixture of diastereoisomers containing predominantly the less stable 10a . Eventual structural identification rests on the X‐ray diffraction analysis of tosylate 18 .