Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-tri

Details Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-tri Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-tri

1995-05-25

1997-05-27

Shah, Mukund J.

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

Organic compounds

Amino nitrogen containing

564387, 564391, 558410, C07C21100, C07C 5116

Patent

active

056334052

ABSTRACT:
An improved synthesis of a highly potent HIV reverse transcription inhibitor is disclosed, involving an acetylide and a trifluoromethyl ketone which produces a chiral product in the presence of a chiral amino alcohol.

REFERENCES:
M.A. Huffman, et al., "Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylidie Addition to Cyclic N-Acyl Ketimines", J. of Org. Chem, vol. 60(6) pp. 1590-1594 (1995).
Patent Abstract of JP4036252A.
K. Soai, et al., "Chiral N,N-Dialkylnorephedrines as Catalysts of the Highly Enantioselective Addition of Dialkylzines to Aliphatic and Aromatic Aldehydes. The Asymmetric Synthesis of Secondary Aliphatic and Aromatic Alcohols of High Optical Purity", J. Org. Chem., vol. 56(13) pp. 4264-4268, (1991).
Patent Abstracts of Japan, vol. 005(020), JP 55 145625, (1981).
O.M. Nefedov, et al., Chem. Abstracts, vol. 89(13), Abs. No. 108235, (1978).
Structure of RN136346-83-3 from J. Org. Chem. USSR, vol. 26 (10.2) vol. 26(10.2), pp. 1902-1904 (1990).
A.S. Thompson, et al., "Use of an Ephedrine Alkoxide to Mediate Enantioselective Addition of an Acetylide to a Prochiral Ketone: Asymmetric Synthesis of the Reverse Transcriptase Inhibitor" L-743,726., Tetrahedron Letts., vol. 36(49) pp. 8937-8940 (1995).
Mukaiyama, et al., "Enantioselective Addition of Acetylene to Aldehyde . . . ", Chemistry Letters, pp. 447-448, 1979.
Mukaiyama, et al., "Asymmetric Addition of Acetylide to Aliphatic Aldehydes . . . ", Chemistry Letters, pp. 255-256, 1980.

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