One-ligand catalytic asymmetric deprotonation of a phosphine borane: Synthesis of P-stereogenic bisphosphine ligands

TY - JOUR

T1 - One-ligand catalytic asymmetric deprotonation of a phosphine borane

T2 - Synthesis of P-stereogenic bisphosphine ligands

AU - Granander, Johan

AU - Secci, Francesco

AU - Canipa, Steven J.

AU - O'Brien, Peter

AU - Kelly, Brian

PY - 2011/6/3

Y1 - 2011/6/3

N2 - A new protocol for the catalytic asymmetric deprotonation of a phosphine borane using s-BuLi and substoichiometric quantities of chiral diamines is reported. The method involves three sequential additions of s-BuLi, and use of (-)-sparteine or the (+)-sparteine surrogate facilitates access to P-stereogenic phosphines with opposite configuration. The method is exemplified by the catalytic asymmetric synthesis of each enantiomer of precursors to QuinoxP*, trichickenfootphos, and Mini-PHOS.

AB - A new protocol for the catalytic asymmetric deprotonation of a phosphine borane using s-BuLi and substoichiometric quantities of chiral diamines is reported. The method involves three sequential additions of s-BuLi, and use of (-)-sparteine or the (+)-sparteine surrogate facilitates access to P-stereogenic phosphines with opposite configuration. The method is exemplified by the catalytic asymmetric synthesis of each enantiomer of precursors to QuinoxP*, trichickenfootphos, and Mini-PHOS.

UR - http://www.scopus.com/inward/record.url?scp=79957855911&partnerID=8YFLogxK

U2 - 10.1021/jo200708e

DO - 10.1021/jo200708e

M3 - Article

AN - SCOPUS:79957855911

SN - 0022-3263

VL - 76

SP - 4794

EP - 4799

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -