SYNTHESIS OF CARBOCYCLES VIA INTRAMOLECULAR CONJUGATE ADDITIONS - ANOTHER SOLUTION TO THE TERPENOID SIDE-CHAIN STEREOCHEMISTRY PROBLEM

Authors
GUEVEL AC HART DJ
Citation
Ac. Guevel et Dj. Hart, SYNTHESIS OF CARBOCYCLES VIA INTRAMOLECULAR CONJUGATE ADDITIONS - ANOTHER SOLUTION TO THE TERPENOID SIDE-CHAIN STEREOCHEMISTRY PROBLEM, Journal of organic chemistry, 61(2), 1996, pp. 465-472
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
2
Year of publication
1996
Pages
465 - 472
Database
ISI
SICI code
0022-3263(1996)61:2<465:SOCVIC>2.0.ZU;2-X
Abstract
Intramolecular conjugate additions of keto esters 7-11, mediated by py rrolidine-acetic acid, provide perhydroindans or bicyclo[6.3.0]undecan es with high levels of diastereoselectivity at the acyclic stereogenic center. Levels of acyclic diastereoselection depend on starting unsat urated ester olefin geometry.