Asymmetric Synthesis of Chiral Spiroketal Bisphosphine Ligands and Their Application in Enantioselective Olefin Hydrogenation

Jian Huang, Mao Hong, Chuan-Chuan Wang, Søren Kramer*, Guo-Qiang Lin, Xing-Wen Sun

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A series of chiral spiroketal bisphosphine ligands containing 1,1'-spirobi(3 H,3' H)isobenzofuran backbones was accessed through asymmetric synthesis and subsequently tested in enantioselective Rh-catalyzed hydrogenation of α-dehydroamino acid esters. The ligand providing the highest enantioselectivity (up to 99.5%) was obtained in seven steps in an overall 38% yield. The synthesis could be performed on a gram scale, and no kinetic resolution of enantiomers is required. Overall, the developed ligand provides an easily accessible alternative to SDP ligands as well as other chiral bisphosphine ligands.
Original languageEnglish
JournalJournal of organic chemistry
Volume83
Issue number20
Pages (from-to)12838-12846
Number of pages9
ISSN0022-3263
DOIs
Publication statusPublished - 2018

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