Catalytic enantioselective cyanosilylation of ketones [14]

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7412-7413

  Hamashima, Yoshitaka ^a   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; SILANE DERIVATIVE;

CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; LETTER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034596326     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001643h     Document Type: Letter

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21. See Supporting Information.
22. For a ligand exchange on titanium from isopropoxide to cyanide by TMSCN, see: Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229-6232.
23. 2O (1 mL) were added. Usual workup and purification by silica gel column chromatography gave the product.
24. The ee was improved to 82% when the reaction was conducted at -60 °C (67% yield for 161 h).
25. 13CN following the reported procedure: Reetz, M. T.; Chatziiosifidis, I. Synthesis 1982, 330.
26. 13CN.
27. Quaternary amino acids are often a component of enzyme inhibitors. See refs 4a.