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N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine.
Org Lett. 2003 Mar 20; 5(6):925-7.OL

Abstract

[reaction: see text] N-Sulfinyl beta-amino Weinreb amides are prepared by condensation of sulfinimines with the potassium enolate of N-methoxy-N-methylacetamide. These new chiral building blocks are useful for the asymmetric synthesis of beta-amino carbonyl compounds, as illustrated here by the concise enantioselective syntheses of sedum alkaloids (+)-sedridine and (-)-allosedridine.

Authors+Show Affiliations

Davis FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Prasad KR
No affiliation info available
Nolt MB
No affiliation info available
Wu Y
No affiliation info available

MeSH

AmidesIndicators and ReagentsMagnetic Resonance SpectroscopyPiperidinesStereoisomerismSulfoxides

Pub Type(s)

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

Language

eng

PubMed ID

12633107

Citation

Davis, Franklin A., et al. "N-sulfinyl Beta-amino Weinreb Amides: Synthesis of Enantiopure Beta-amino Carbonyl Compounds. Asymmetric Synthesis of (+)-sedridine and (-)-allosedridine." Organic Letters, vol. 5, no. 6, 2003, pp. 925-7.
Davis FA, Prasad KR, Nolt MB, et al. N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine. Org Lett. 2003;5(6):925-7.
Davis, F. A., Prasad, K. R., Nolt, M. B., & Wu, Y. (2003). N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine. Organic Letters, 5(6), 925-7.
Davis FA, et al. N-sulfinyl Beta-amino Weinreb Amides: Synthesis of Enantiopure Beta-amino Carbonyl Compounds. Asymmetric Synthesis of (+)-sedridine and (-)-allosedridine. Org Lett. 2003 Mar 20;5(6):925-7. PubMed PMID: 12633107.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine. AU - Davis,Franklin A, AU - Prasad,Kavirayani R, AU - Nolt,M Brad, AU - Wu,Yongzhong, PY - 2003/3/14/pubmed PY - 2003/6/21/medline PY - 2003/3/14/entrez SP - 925 EP - 7 JF - Organic letters JO - Org Lett VL - 5 IS - 6 N2 - [reaction: see text] N-Sulfinyl beta-amino Weinreb amides are prepared by condensation of sulfinimines with the potassium enolate of N-methoxy-N-methylacetamide. These new chiral building blocks are useful for the asymmetric synthesis of beta-amino carbonyl compounds, as illustrated here by the concise enantioselective syntheses of sedum alkaloids (+)-sedridine and (-)-allosedridine. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12633107/N_sulfinyl_beta_amino_Weinreb_amides:_synthesis_of_enantiopure_beta_amino_carbonyl_compounds__Asymmetric_synthesis_of__+__sedridine_and_____allosedridine_ DB - PRIME DP - Unbound Medicine ER -