Diastereoselective Chelation-Controlled Additions to β-Silyloxy Aldehydes

A general diastereoselective method for the addition of dialkylzincs and (E)-di- and (E)-trisubstituted vinylzinc reagents to β-silyloxy aldehydes is presented. This method employs alkyl zinc triflate and nonaflate Lewis acids and affords chelation-controlled products (6:1 to > 20:1 dr).

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Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2012-07, Vol.14 (13), p.3368-3371
Hauptverfasser:	Stanton, Gretchen R, Kauffman, Meara C, Walsh, Patrick J
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols - chemical synthesis Alcohols - chemistry Aldehydes - chemistry Chelating Agents - chemistry Molecular Structure Organometallic Compounds - chemistry Stereoisomerism Zinc - chemistry
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Beschreibung
Zusammenfassung:	A general diastereoselective method for the addition of dialkylzincs and (E)-di- and (E)-trisubstituted vinylzinc reagents to β-silyloxy aldehydes is presented. This method employs alkyl zinc triflate and nonaflate Lewis acids and affords chelation-controlled products (6:1 to > 20:1 dr).
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol301354w