Chiral Terpene Auxiliaries V: Synthesis of New Chiral γ-hydroxyphosphine Oxides Derived from α-pinene

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2019 Nov 16

PMID 31728163

Authors

Anna Kmieciak

Marek P Krzeminski

Affiliations

Soon will be listed here.

Abstract

New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1,2,4,5)-3-methyleneneoisoverbanol and (1,2,3,5)-4-methyleneneoisopinocampheol, to allylphosphine oxides. Hydroxy groups were introduced stereoselectively through a hydroboration-oxidation reaction proceeding from the less hindered site providing a relationship between the hydroxy and the phosphine substituents.

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