title: Hydrophosphination of propargylic alcohols and amines with phosphine boranes.
abstract: The first uncatalyzed hydrophosphinations of propargylic amines and alcohols with phosphine- borane complexes are described. The reactions proceed at ambient temperature or below without the use of protecting groups or the need to handle pyrophoric secondary phosphines, furnishing air-stable phosphineborane-amines and alcohols in good yields. Utilization of chiral propargylic substrates and unsymmetrical secondary phosphineboranes leads to diastereomeric P-chiral products that can be separated by fractional crystallization or chromatography. Initial applications of these new P-X species to asymmetric catalysis are detailed.
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: Guijun
authors: G
authors: Wang
authors: Peter
authors: P
authors: Wipf
authors: Chris H
authors: CH
authors: Senanayake
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000588:Amines; D001880:Boranes; D010720:Phosphines; D020005:Propanols; C028255:propargyl alcohol