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Synlett 2011(7): 919-922  
DOI: 10.1055/s-0030-1259710
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Copper-Catalyzed O-H Insertion of α-Diazo Phosphonates

Shou-Fei Zhu, Wang-Qiao Chen, Qian-Qian Zhang, Hong-Xiang Mao, Qi-Lin Zhou*
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
Fax: +86(22)23506177; e-Mail: qlzhou@nankai.edu.cn;
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Publication History

Received 19 November 2010
Publication Date:
08 March 2011 (online)

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Abstract

A copper-catalyzed asymmetric O-H insertion of α-di­azo phosphonates with alcohols by using chiral spiro bisoxazoline ligands was developed. The insertion reaction exhibited good yields (up to 89%) with high enantioselectivities (up to 98% ee) and provided an efficient approach for synthesis of enantiomerically enriched α-alkoxy and hydroxy phosphonate derivatives starting from readily available materials.

Key words

asymmetric O-H insertion - chiral spiro ligands - copper catalysts - α-diazo phosphonates - α-alkoxy phosphonates

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8

NaBArF = sodium tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate.

9

Box = 2,2′-(1-methylethyliene)bis(4,5-dihydro-4-tert-butyloxazole).

10

Pybox = 2,6-bis(4,5-dihydro-4-isopropyloxazole)pyridine.