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Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides.
J Org Chem. 2005 Mar 18; 70(6):2184-90.JO

Abstract

[reaction: see text] Diverse organometallic reagents readily add to enantiopure N-sulfinyl beta-amino Weinreb amides providing the corresponding, stable, N-sulfinyl beta-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of beta-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters.

Authors+Show Affiliations

Davis FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Nolt MB
No affiliation info available
Wu Y
No affiliation info available
Prasad KR
No affiliation info available
Li D
No affiliation info available
Yang B
No affiliation info available
Bowen K
No affiliation info available
Lee SH
No affiliation info available
Eardley JH
No affiliation info available

MeSH

AldehydesAmidesKetonesMolecular ConformationStereoisomerismSulfoxides

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15760203

Citation

Davis, Franklin A., et al. "Asymmetric Synthesis of Beta-amino Carbonyl Compounds With N-sulfinyl Beta-amino Weinreb Amides." The Journal of Organic Chemistry, vol. 70, no. 6, 2005, pp. 2184-90.
Davis FA, Nolt MB, Wu Y, et al. Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides. J Org Chem. 2005;70(6):2184-90.
Davis, F. A., Nolt, M. B., Wu, Y., Prasad, K. R., Li, D., Yang, B., Bowen, K., Lee, S. H., & Eardley, J. H. (2005). Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides. The Journal of Organic Chemistry, 70(6), 2184-90.
Davis FA, et al. Asymmetric Synthesis of Beta-amino Carbonyl Compounds With N-sulfinyl Beta-amino Weinreb Amides. J Org Chem. 2005 Mar 18;70(6):2184-90. PubMed PMID: 15760203.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides. AU - Davis,Franklin A, AU - Nolt,M Brad, AU - Wu,Yongzhong, AU - Prasad,Kavirayani R, AU - Li,Danyang, AU - Yang,Bin, AU - Bowen,Kerisha, AU - Lee,Seung H, AU - Eardley,John H, PY - 2005/3/12/pubmed PY - 2005/6/9/medline PY - 2005/3/12/entrez SP - 2184 EP - 90 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 6 N2 - [reaction: see text] Diverse organometallic reagents readily add to enantiopure N-sulfinyl beta-amino Weinreb amides providing the corresponding, stable, N-sulfinyl beta-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of beta-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15760203/Asymmetric_synthesis_of_beta_amino_carbonyl_compounds_with_N_sulfinyl_beta_amino_Weinreb_amides_ DB - PRIME DP - Unbound Medicine ER -