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Enantioselective Horner–Wadsworth–Emmons reaction for the asymmetric synthesis of α-fluoro-α,β-unsaturated esters

✍ Scribed by Shigeki Sano; Kenji Yokoyama; Rie Teranishi; Motoo Shiro; Yoshimitsu Nagao

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
106 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The enantioselective Horner-Wadsworth-Emmons reaction of 2-fluoro-2-diethylphosphonoacetates with s-symmetric prochiral 2-substituted-1,3-dioxan-5-ones and 4-substituted-cyclohexanones was investigated by employing Sn(OSO 2 CF 3 ) 2 and N-ethylpiperidine in the presence of an external chiral ligand, (S)-(-)-1-methyl-2-(1-piperidinomethyl)pyrrolidine. A chiral a-fluoro-a,b-unsaturated ester was obtained in up to 80% ee.

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