3 years ago

Synthesis of P-Chiral Dihydrobenzooxaphosphole Core for BI Ligands in Asymmetric Transformations

Synthesis of P-Chiral Dihydrobenzooxaphosphole Core for BI Ligands in Asymmetric Transformations
Xiao-jun Wang, Zhulin Tan, Jon C. Lorenz, Xudong Wei, Guisheng Li, Philomen DeCroos, Nelu Grinberg, Nathan K. Yee, Chris H. Senanayake, Yongda Zhang
An efficient and practical synthesis of enantiomerically pure P-chiral dihydrobenzooxaphosphole (BOP) core 1 is developed that is amenable to large scale preparation of the related ligand series. The unique epimerization of the P-chiral center of the undesired (R,R)-diastereomeric phosphine oxide 19 through chlorination followed by crystallization makes this chemical resolution method achieve 65% yield of desired (R,S)-diastereomer 12.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00491

DOI: 10.1021/acs.joc.7b00491

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