Stereochemistry of conjugate addition to 4- and 5-substituted α,β-unsaturated δ-lactones

Autor:	Ian Fleming, Ken Takaki, Anne C. Ware, N. Laxma Reddy
Rok vydání:	1987
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Addition reaction Silylation chemistry Stereochemistry Reagent Cyclohexane conformation Hydroxy group Lactam Molecular Medicine Lactone Conjugate
Zdroj:	J. Chem. Soc., Chem. Commun.. :1472-1474
ISSN:	0022-4936
DOI:	10.1039/c39870001472
Popis:	Conjugate addition, especially of the phenyldimethylsilylcuprate reagent, to 4- and 5-substituted α,β-unsaturated δ-lactones [(5) and (18)] is highly selective for the formation of the trans-products [(6), (7), (9), (10), and (19)], the silicon-containing products having 1H n.m.r. coupling constants indicative of distortions from the chair conformation; the silyl group can be converted into a hydroxy group to give the lactones (8) and (20).
Databáze:	OpenAIRE
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