Regioselective Semihydrogenation of Dienes

A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimin...

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Veröffentlicht in:	Journal of organic chemistry 2011-05, Vol.76 (10), p.4132-4138
Hauptverfasser:	Graham, Thomas J. A, Poole, Thomas H, Reese, Charles N, Goess, Brian C
Format:	Artikel
Sprache:	eng
Schlagworte:	Aliphatic compounds Chemistry Exact sciences and technology Organic chemistry Preparations and properties
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo200262r