Tags

Type your tag names separated by a space and hit enter

Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives.
Org Lett. 2005 Mar 03; 7(5):921-4.OL

Abstract

A new, facile, and highly stereoselective protocol toward alpha,beta-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples. [reaction: see text]

Authors+Show Affiliations

Chen D
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
Guo L
No affiliation info available
Liu J
No affiliation info available
Kirtane S
No affiliation info available
Cannon JF
No affiliation info available
Li G
No affiliation info available

MeSH

Amino AcidsCatalysisCombinatorial Chemistry TechniquesEstersIndicators and ReagentsKetonesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15727475

Citation

Chen, Dianjun, et al. "Functionalization of Alpha,beta-unsaturated Esters and Ketones: a Facile and Highly Stereoselective One-pot Approach to N-protected Alpha,beta-dehydroamino Acid Derivatives." Organic Letters, vol. 7, no. 5, 2005, pp. 921-4.
Chen D, Guo L, Liu J, et al. Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives. Org Lett. 2005;7(5):921-4.
Chen, D., Guo, L., Liu, J., Kirtane, S., Cannon, J. F., & Li, G. (2005). Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives. Organic Letters, 7(5), 921-4.
Chen D, et al. Functionalization of Alpha,beta-unsaturated Esters and Ketones: a Facile and Highly Stereoselective One-pot Approach to N-protected Alpha,beta-dehydroamino Acid Derivatives. Org Lett. 2005 Mar 3;7(5):921-4. PubMed PMID: 15727475.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives. AU - Chen,Dianjun, AU - Guo,Li, AU - Liu,Junying, AU - Kirtane,Sameer, AU - Cannon,John F, AU - Li,Guigen, PY - 2005/2/25/pubmed PY - 2005/12/13/medline PY - 2005/2/25/entrez SP - 921 EP - 4 JF - Organic letters JO - Org Lett VL - 7 IS - 5 N2 - A new, facile, and highly stereoselective protocol toward alpha,beta-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15727475/Functionalization_of_alphabeta_unsaturated_esters_and_ketones:_a_facile_and_highly_stereoselective_one_pot_approach_to_N_protected_alphabeta_dehydroamino_acid_derivatives_ DB - PRIME DP - Unbound Medicine ER -