Myrtenal and Myrtanal as Auxiliaries in the Synthesis of Some C,P-Stereogenic Hydroxyphosphine Oxides and Hydroxyphosphine-Boranes Possessing up to Four Contiguous Centers of Chirality

Author:

Pietrusiewicz K. Michał1ORCID,Kozioł Anna E.1ORCID,Małuszyńska Hanna2,Sowa Sylwia1ORCID

Affiliation:

1. Department of Organic Chemistry and Crystallochemistry, Faculty of Chemistry, Institute of Chemical Sciences, Maria Curie-Sklodowska University, 20-614 Lublin, Poland

2. Radiospectroscopy Division, Faculty of Physics, Adam Mickiewicz University, 61-614 Poznan, Poland

Abstract

1,4- and 1,2-additons of secondary phosphine oxides to (1R)-myrtenal and (1S)-myrtanal were evaluated as potential routes to P,C-stereogenic phosphine oxides bearing additional hydroxyl or aldehyde functions. 1,4-Additions of racemic secondary phosphine oxides to (1R)-myrtenal were found to offer moderate to good stereoselectivity which shows some promise for utility in kinetic resolution processes, especially at lower conversions. In case of 1,2-additions making the process doubly asymmetric by using an enantiomerically pure secondary phosphine oxide as substrate turned out to be practical. The stereochemical course of the addition reactions under study is presented. The P-resolved 1,2-addition products were demonstrated to undergo facile reduction by BH3 at room temperature leading to the formation of the corresponding α-hydroxyphosphine-boranes with clean inversion of configuration at the P-centre. All P,C-stereogenic phosphine oxides and boranes that were isolated in the form of a single diastereoisomer were assigned their absolute configurations by means of X-ray crystallography and/or 2D NMR spectral techniques.

Funder

Ministry of Science and Higher Education

Publisher

MDPI AG

Subject

Physics and Astronomy (miscellaneous),General Mathematics,Chemistry (miscellaneous),Computer Science (miscellaneous)

Reference41 articles.

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5. Enantioselective catalysis with chiral phosphine oxide preligands;Dubrovina;Angew. Chem. Int. Ed.,2004

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