Chiral P-Heterocycles: Efficient Method for the Resolution of 3-Methyl-3-phospholene 1-Oxides

Abstract

The enantiomers of 1-aryl-, 1-alkyl- and 1-alkoxy-3-methyl-3-phospholene 1-oxides were separated in good yields and in high enantiomeric excesses (up to > 99% ee) by resolution via formation of diastereomeric complexes with (–)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane (TADDOL) or (–)-(2R,3R)-α,α,α′,α′-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol.

Keywords:

• Chiral P-heterocycles
• diastereomeric complex formation
• resolution
• TADDOL

Acknowledgments

The authors are grateful for the financial support from the Hungarian Scientific Research Fund (OTKA, Grants No. T 067679 and T 042725). TN is a recipient of a Bolyai fellowship.

Notes

* for the 1:2 complex formed by the use of one equivalent of 3.