title: [2,3]-Sigmatropic rearrangements of 2-phosphineborane 2-propen-1-ols: rapid access to enantioenriched diphosphine monoxide derivatives.
abstract: 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.
authors: Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, USA. carl.busacca@boehringer-ingelheim.com
authors: Carl A
authors: CA
authors: Busacca
authors: Bo
authors: B
authors: Qu
authors: Elisa
authors: E
authors: Farber
authors: Nizar
authors: N
authors: Haddad
authors: Nicole
authors: N
authors: Grět
authors: Anjan K
authors: AK
authors: Saha
authors: Magnus C
authors: MC
authors: Eriksson
authors: Jiang-Ping
authors: JP
authors: Wu
authors: Keith R
authors: KR
authors: Fandrick
authors: Steve
authors: S
authors: Han
authors: Nelu
authors: N
authors: Grinberg
authors: Shengli
authors: S
authors: Ma
authors: Heewon
authors: H
authors: Lee
authors: Zhibin
authors: Z
authors: Li
authors: Michael
authors: M
authors: Spinelli
authors: Austin
authors: A
authors: Gold
authors: Zhuzhu
authors: Z
authors: Wang
authors: Guijun
authors: G
authors: Wang
authors: Peter
authors: P
authors: Wipf
authors: Chris H
authors: CH
authors: Senanayake
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009943:Organophosphorus Compounds; D020005:Propanols; C006463:allyl alcohol