title: One-pot process that efficiently generates single stereoisomers of 1,3-bisphosphinylpropanes having five chiral centers.
abstract: P,C-stereogenic 1,3-bisphosphinylpropanes 3 that have up to five stereogenic centers could be obtained stereoselectively in high yields by a one-step reaction of (RP)-menthylphenylphosphine oxide 1 with α,β-unsaturated aldehydes 2 catalyzed by KOH at room temperature. A mechanism was proposed as to involve a stereoselective intermolecular 1,3'-phosphorus migration from the 1,2-adduct of 1 with 2 to another 2 generating a 1,4-adduct that subsequently reacts with 1 to produce 3.
authors.affiliation: College of Chemistry and Chemical Engineering, Liaocheng University , Liaocheng, Shandong 252059, China.
authors.forename: He
authors.initials: H
authors.lastname: Zhang
authors.forename: Yong-Ming
authors.initials: YM
authors.lastname: Sun
authors.forename: Yalei
authors.initials: Y
authors.lastname: Zhao
authors.forename: Zhong-Yang
authors.initials: ZY
authors.lastname: Zhou
authors.forename: Ji-Ping
authors.initials: JP
authors.lastname: Wang
authors.forename: Nana
authors.initials: N
authors.lastname: Xin
authors.forename: Shao-Zhen
authors.initials: SZ
authors.lastname: Nie
authors.forename: Chang-Qiu
authors.initials: CQ
authors.lastname: Zhao
authors.forename: Li-Biao
authors.initials: LB
authors.lastname: Han
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D011407:Propane / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D010721:Phosphinic Acids; D011407:Propane