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[2,3]-Sigmatropic Rearrangements of 2‑Phosphineborane 2‑Propen-1-ols: Rapid Access to Enantioenriched Diphosphine Monoxide Derivatives

Busacca, Carl A ; Qu, Bo ; Farber, Elisa ; Haddad, Nizar ; Grět, Nicole ; Saha, Anjan K ; Eriksson, Magnus C ; Wu, Jiang-Ping ; Fandrick, Keith R ; Han, Steve ; Grinberg, Nelu ; Ma, Shengli ; Lee, Heewon ; Li, Zhibin ; Spinelli, Michael ; Gold, Austin ; Wang, Zhuzhu ; Wang, Guijun ; Wipf, Peter ; Senanayake, Chris H

Organic letters, 2013-03, Vol.15 (5), p.1136-1139 [Periódico revisado por pares]

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Título:
[2,3]-Sigmatropic Rearrangements of 2‑Phosphineborane 2‑Propen-1-ols: Rapid Access to Enantioenriched Diphosphine Monoxide Derivatives
Autor: Busacca, Carl A ; Qu, Bo ; Farber, Elisa ; Haddad, Nizar ; Grět, Nicole ; Saha, Anjan K ; Eriksson, Magnus C ; Wu, Jiang-Ping ; Fandrick, Keith R ; Han, Steve ; Grinberg, Nelu ; Ma, Shengli ; Lee, Heewon ; Li, Zhibin ; Spinelli, Michael ; Gold, Austin ; Wang, Zhuzhu ; Wang, Guijun ; Wipf, Peter ; Senanayake, Chris H
Assuntos: Catalysis ; Combinatorial Chemistry Techniques ; Molecular Structure ; Organophosphorus Compounds - chemical synthesis ; Organophosphorus Compounds - chemistry ; Propanols - chemistry ; Stereoisomerism
É parte de: Organic letters, 2013-03, Vol.15 (5), p.1136-1139
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: Hydrophosphination of secondary propargylic alcohols generates phosphine-containing allylic alcohols that undergo facile [2,3]-sigmatropic rearrangements with chlorophosphines, furnishing highly enantioenriched, crystalline diphosphine monoxides. The configuration at the newly formed stereocenter is opposite to that expected based on prior studies, and an ab initio computational evaluation of the possible transition states was performed to help explain the stereochemical course of the reaction.
Editor: United States: American Chemical Society
Idioma: Inglês

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