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Study of the Diastereoselectivity of Cobalt‐Mediated [2+2+2] Cycloadditions of Substituted Linear Enediyne Esters
Author(s) -
Slowinski Franck,
Aubert Corinne,
Malacria Max
Publication year - 2001
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 - 10.1002/1099-0690(200109)2001:18<3491::aid-ejoc3491>3.0.co;2-3
Subject(s) - enediyne , chemistry , substituent , alkyne , stereochemistry , alkene , diastereomer , cobalt , organic chemistry , catalysis
The preparation of substituted linear enediyne esters bearing the double bond either at the terminal or at internal position and the ester substituent either at the alkyne or at the alkene terminus is presented. Their cobalt(I)‐mediated [2+2+2] cyclizations produce the η 4 ‐complexed tricyclic compounds in very good yields. The endo / exo selectivity depends on the position of the ester in the enediyne, but the cyclization can be totally diastereoselective. The asymmetric induction in the cyclization of enediynes bearing chiral esters has been studied; however, the diastereomeric excesses are low.