Process for the production of (2R,3E)-4-halo-3-buten-2-ols

Details Process for the production of (2R,3E)-4-halo-3-buten-2-ols Process for the production of (2R,3E)-4-halo-3-buten-2-ols

1992-11-05

1993-10-19

Lone, Werren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568840, 568841, C07C 3342

Patent

active

052547566

ABSTRACT:
(2R,3E)-4-halo-3-buten-2-ols are produced by kinetic resolution of racemates from the corresponding racemates. The racemate is esterified by reaction with a carboxylic acid derivative, preferably with chloroacetyl chloride. Then the (R)-ester is enantioselectively hydrolyzed with a lipase from Pseudomonas fluorescens. The corresponding (2R,3E)-4-halo-3-buten-2-ol also can be obtained from the remaining (S)-ester after separation. The compounds are chiral synthesis structural elements for the production of optically active natural substances.

REFERENCES:
F.-T. Luo and E.-I. Negishi, J. Org. Chem., 50 (1985), pp. 4762 to 4766.
T. Ito et al., Tetrahedron Lett., 30, (1989), pp. 7083 to 7086.
Y. Kitano et al., Tetrahedron Lett., 28, (1987), pp. 6351 to 6354.
W. B. Benson, J. Org. Chem., 29, (1964), p. 385.
Rompp Chemie-Lexikon, 9th Edition, vol. 5 (1992), p. 4135.

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