Is it possible to estimate the enantioselectivity of a chiral catalyst from its racemic mixture?

Journal of the American Chemical Society

Volumn 125, Issue 25, 2003, Pages 7490-7491

  Lagasse, Franz ^a   Tsukamoto, Masaki ^a   Welch, Christopher J ^b   Kagan, Henri B ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIKETONE;

ANALYTIC METHOD; ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; RACEMIC MIXTURE; REACTION ANALYSIS; REDUCTION;

EID: 0038208276     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0300315     Document Type: Article

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25. homo = 28, THF, 66 °C), ruling out a strong substrate control in the second reduction (for details, see Supporting Information).
26. homo is quite low (51%) because of the competitive direct formation of monoalkoxyborane, followed by uncatalyzed intramolecular reduction.
27. 3 (THF, 0 °C). Ketol 2 was recovered (racemic), and a 1:1 mixture of (S,S)-3 (92% ee) and meso-3 was obtained.