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On the Stereochemistry of Organocopper Mediated Conversion of Propargylic Esters to Allenes
Author(s) -
Haces Alberto,
van Kruchten Eugène M.G.A.,
Okamura William H.
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500084
Subject(s) - chemistry , reagent , cuprate , stereochemistry , allene , medicinal chemistry , organic chemistry , catalysis , physics , optoelectronics , doping
Using a vitamin D‐related steroidal CD fragment as a stereochemical probe, the effect of various factors on the stereochemical course of the organocopper induced conversion of propargylic esters to allenes has been studied. In all cases, an anti mode of attack by the organocopper species was found to be preferred. The effectiveness of Gilman‐type reagents (R 2 CuLi) versus that of the Lipshutz‐type higher‐order mixed cuprate systems (R 2 CuCNLi 2 ) in promoting the reaction was also studied.