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A New Route to trans ‐Substituted γ‐Lactones
Author(s) -
Kunz Thomas,
Reissig HansUlrich
Publication year - 1988
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.198802681
Subject(s) - reagent , selectivity , chemistry , medicinal chemistry , stereochemistry , organic chemistry , computational chemistry , catalysis
trans ‐Substituted γ‐lactones are formed with high diastereoselectivity according to Equation (a), especially when cuprates are used as organometallic reagents. For allyltrimethylsilane/TiCl 4 , the selectivity is only large when R 1 is a bulky group. The γ‐lactones thus obtained are valuable synthetic intermediates, and their formation is of mechanistic interest since they can be used to test the validity of the Felkin–Ahn model (R 1 = Me, i Pr, Ph; R 2 = Me, n Bu, allyl).