+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Enantioselective Horner-Wadsworth-Emmons reaction for the asymmetric synthesis of alpha-fluoro-alpha,beta-unsaturated esters

Enantioselective Horner-Wadsworth-Emmons reaction for the asymmetric synthesis of alpha-fluoro-alpha,beta-unsaturated esters

Tetrahedron Letters 43(2): 281-284, 7 January

The enantioselective Horner-Wadsworth-Emmons reaction of 2-fluoro-2-diethylphosphonoacetates with sigma-symmetric prochiral 2-substituted-1,3-dioxan-5-ones and 4-substituted-cyclohexanones was investigated by employing Sn(OSO2CF3)2 and N-ethylpiperidine in the presence of an external chiral ligand, (S)-(-)-1-methyl-2-(1-piperidinomethyl)pyrrolidine. A chiral alpha-fluoro-alpha,beta-unsaturated ester was obtained in up to 80% ee.

Please choose payment method:

(PDF emailed within 1 workday: $29.90)

Accession: 010582146

Download citation: RISBibTeXText

Related references

Organocatalytic sequential alpha-amination-Horner-Wadsworth-Emmons olefination of aldehydes: enantioselective synthesis of gamma-amino-alpha,beta-unsaturated esters. Organic Letters 9(6): 1001-1004, 2007

A novel intramolecular Horner-Wadsworth-Emmons reaction A simple and general route to alpha fluoro-alpha,beta-unsaturated diesters. Journal of Organic Chemistry 59(23): 7085-7091, 1994

An efficient procedure based on a MW-assisted Horner-Wadsworth-Emmons reaction for the synthesis of (Z)-3,3-trisubstituted-alpha,beta-unsaturated esters. Molecules 15(9): 5928-5942, 2011

New Reaction Mode of the Horner-Wadsworth-Emmons Reaction for the Preparation of α-Fluoro-α,β-unsaturated Esters. Synlett 1998(7): 777-779, 1998

Enantioselective synthesis of syn/anti-1,3-amino alcohols via proline-catalyzed sequential alpha-aminoxylation/alpha-amination and Horner-Wadsworth-Emmons olefination of aldehydes. Organic Letters 12(12): 2762-2765, 2010

Enantioselective preparation of allenecarboxylates by asymmetric Horner-Wadsworth-Emmons reaction. Tetrahedron Letters 37(21): 3735-3738, 1996

Highly stereoselective synthesis of (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters and (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated amides from 1-bromo-1-fluoroalkenes via palladium-catalyzed carbonylation reactions. Journal of Organic Chemistry 70(11): 4346-4353, 2005

Z-selective olefination of base-sensitive chiral beta-hydroxy-alpha-aminoaldehydes using a modified Horner-Wadsworth-Emmons reaction. Tetrahedron 53(5): 1707-1714, 1997

A Catalytic Michael/Horner-Wadsworth-Emmons Cascade Reaction for Enantioselective Synthesis of Thiochromenes. Advanced Synthesis & Catalysis 355(10): 1989-1995, 2013

Chemical Synthesis of the Epimeric (23R)- and (23S)-Fluoro Derivatives of Bile Acids via Horner-Wadsworth-Emmons Reaction. Lipids 50(9): 919-926, 2016

A novel reaction of beta,beta'-dihydroxy acids or esters with vanadium(V) trichloride oxide. New entry to the stereoselective synthesis of alpha-fluoro-alpha,beta-unsaturated acids and esters. Tetrahedron Letters 39(27): 4865-4868, 1998

Catalytic enantioselective synthesis of quaternary all-carbon stereogenic centers. Preparation of alpha,alpha'-disubstituted beta,gamma-unsaturated esters through Cu-catalyzed asymmetric allylic alkylations. Organic Letters 7(7): 1255-1258, 2005

Z-selective formation of trisubstituted alpha,beta-unsaturated nitrile by the horner-emmons reaction. Tetrahedron Letters 35(10): 1581-1584, 1994

Catalytic asymmetric Roskamp reaction of alpha-alkyl-alpha-diazoesters with aromatic aldehydes: highly enantioselective synthesis of alpha-alkyl-beta-keto esters. Journal of the American Chemical Society 132(25): 8532-8533, 2010

Asymmetric Synthesis of the Diene Unit of Methyl Sartortuoate via a Temperature-Sensitive Intramolecular Horner-Wadsworth-Emmons (HWE) Reaction. Synlett 2007(4): 0571-0574, 2007