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Stereoselective enol tosylation: preparation of trisubstituted alpha,beta-unsaturated esters.
Org Lett. 2005 Jan 20; 7(2):215-8.OL

Abstract

[Reaction: see text] The stereoselective preparation of (E)- or (Z)-trisubstituted alpha,beta-unsaturated esters in three steps from N-protected glycine is presented. The key step in the synthesis is the highly selective enol tosylation of gamma-amino beta-keto esters. The enol tosylates are stable, crystalline compounds that undergo smooth and effective Suzuki-Miyaura coupling reaction with a variety of aryl boronic acids.

Authors+Show Affiliations

Baxter JM
Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. jenny_baxter@merck.com
Steinhuebel D
No affiliation info available
Palucki M
No affiliation info available
Davies IW
No affiliation info available

MeSH

AldehydesEstersGlycineKetonesMolecular StructureStereoisomerismTosyl Compoundsgamma-Aminobutyric Acid

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15646961

Citation

Baxter, Jenny M., et al. "Stereoselective Enol Tosylation: Preparation of Trisubstituted Alpha,beta-unsaturated Esters." Organic Letters, vol. 7, no. 2, 2005, pp. 215-8.
Baxter JM, Steinhuebel D, Palucki M, et al. Stereoselective enol tosylation: preparation of trisubstituted alpha,beta-unsaturated esters. Org Lett. 2005;7(2):215-8.
Baxter, J. M., Steinhuebel, D., Palucki, M., & Davies, I. W. (2005). Stereoselective enol tosylation: preparation of trisubstituted alpha,beta-unsaturated esters. Organic Letters, 7(2), 215-8.
Baxter JM, et al. Stereoselective Enol Tosylation: Preparation of Trisubstituted Alpha,beta-unsaturated Esters. Org Lett. 2005 Jan 20;7(2):215-8. PubMed PMID: 15646961.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective enol tosylation: preparation of trisubstituted alpha,beta-unsaturated esters. AU - Baxter,Jenny M, AU - Steinhuebel,Dietrich, AU - Palucki,Michael, AU - Davies,Ian W, PY - 2005/1/14/pubmed PY - 2006/7/6/medline PY - 2005/1/14/entrez SP - 215 EP - 8 JF - Organic letters JO - Org Lett VL - 7 IS - 2 N2 - [Reaction: see text] The stereoselective preparation of (E)- or (Z)-trisubstituted alpha,beta-unsaturated esters in three steps from N-protected glycine is presented. The key step in the synthesis is the highly selective enol tosylation of gamma-amino beta-keto esters. The enol tosylates are stable, crystalline compounds that undergo smooth and effective Suzuki-Miyaura coupling reaction with a variety of aryl boronic acids. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15646961/Stereoselective_enol_tosylation:_preparation_of_trisubstituted_alphabeta_unsaturated_esters_ DB - PRIME DP - Unbound Medicine ER -