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Asymmetric Synthesis of (S)-5,5,5,5′,5′,5′,5′-Hexafluoroleucine (1998)

Zhang, Cong ; Ludin, Christian ; Eberle, Marcel K. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 81 (1998), S. 174-181

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: (S)-5,5,5,5′,5′,5′-Hexafluoroleucine ((S)-13) of 81 % ee is prepared from hexafluoroacetone (l) and ethyl bromopyruvate (= ethyl 2-oxopropanoate) in 7 steps with an overall yield of 18% (Schemes 1 and 2). Key step in this sequence is the highly enantioselective reduction of the carbonyl group in α-keto ester 4 either by bakers' yeast (91 % ee) or by ‘catecholborane’ 6 utilizing an oxazaborolidine catalyst, yielding hydroxy ester (R)-5 with 99% ee. The absolute configuration was determined by X-ray analysis of the HCl adduct (S,R)-9b of (2S)-N-[(R)- l-phenylethyl]-5,5,5,5′,5′,5′-hexafluoroleucine ethyl ester.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19980810116

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