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Asymmetric trimethylsilylcyanation of aldehydes utilizing chiral bismuth compounds. A frontier in bismuth mediated synthetic reactions

Wada, Makoto, Takahashi, Toshikazu, Domae, T., Fukuma, T., Miyoshi, N. and Smith, Keith 1997. Asymmetric trimethylsilylcyanation of aldehydes utilizing chiral bismuth compounds. A frontier in bismuth mediated synthetic reactions. Tetrahedron: Asymmetry 8 (23) , pp. 3939-3946. 10.1016/S0957-4166(97)00570-3

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Abstract

Bismuth(III) chloride (BiCl3) was found to work efficiently as a versatile catalyst for cyanation of aldehydes with trimethylsilyl cyanide to afford the corresponding cyanohydrins in high yields. Triphenylbismuthan (Ph3Bi) is also effective. The reaction has been applied to the asymmetric cyanation of a variety of aldehydes in high yields with moderate to good enantioselectivities by use of a chiral bismuth catalyst prepared in situ from BiCl3 and (2R,3R)-(+)-diethyl tartrate.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Elsevier
ISSN: 0957-4166
Last Modified: 04 Jun 2017 03:14
URI: http://orca.cf.ac.uk/id/eprint/18541

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