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

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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564184, 564218, 564391, C07C21100, C07C 5116

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active

056987412

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:
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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).
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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).

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