An intramolecular cyclization approach to optically active cyclopentenyl bromides

Autor:	Stephane Borrelly, Leo A. Paquette
Rok vydání:	1993
Předmět:	chemistry.chemical_compound chemistry Trimethylsilyl Stereochemistry Organic Chemistry Proton NMR Cyclopentene Halogenation Enantiomer Propargyl alcohol Cycloalkene Dextrorotatory
Zdroj:	The Journal of Organic Chemistry. 58:2714-2717
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00062a011
Popis:	The two antipodes of 1-bromo-3,3-dimethyl-4-[(tert-butyldimethylsilyl)oxy] cyclopentene, the dextrorotatory form of which (1) is regarded as a potential synthetic precursor to kalmanol, have been prepared in a state of high enantiomeric purity from propargyl alcohol. The key steps in the abbreviated synthetic pathway involve the bromination-dehydrobromination of 3-(trimethylsilyl)propenal 12 to give 2-bromo-3-(trimethylsilyl)propenal 7, the conversion of 2-bromo-3-(trimethylsilyl)propen-1-ol 13 to the 1-bromo-3,3-dimethylcyclopenten-4-ol 18 by a novel tandem Claisen-Sakurai reaction sequence, and efficient enzymatic resolution of 18 via its chloroacetate ester. The absolute configurational assignments are based on 1 H NMR analyses of the (R)- and (S)-MTPA esters of (-)-20
Databáze:	OpenAIRE
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