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Asymmetric synthesis of alpha-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline.
Org Lett. 2004 Sep 16; 6(19):3393-5.OL

Abstract

[reaction: see text] N-Sulfinyl alpha-amino 1,3-dithioketals are prepared in high de and good yield by treating sulfinimines with lithio-1,3-dithianes. Selective removal of the N-sulfinyl or the thioketal groups affords stable alpha-amino 1,3-dithioketals and N-sulfinyl alpha-amino ketones, respectively. This new sulfinimine-derived chiral building block is employed in the asymmetric synthesis of polyoxypeptin amino acid (2S,3R)-(-)-3-hydroxy-3-methylproline.

Authors+Show Affiliations

Davis FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Ramachandar T
No affiliation info available
Liu H
No affiliation info available

MeSH

CatalysisIndicators and ReagentsMolecular StructureProlineStereoisomerismSulfur Compounds

Pub Type(s)

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

Language

eng

PubMed ID

15355060

Citation

Davis, Franklin A., et al. "Asymmetric Synthesis of Alpha-amino 1,3-dithioketals From Sulfinimines (N-sulfinyl Imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline." Organic Letters, vol. 6, no. 19, 2004, pp. 3393-5.
Davis FA, Ramachandar T, Liu H. Asymmetric synthesis of alpha-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline. Org Lett. 2004;6(19):3393-5.
Davis, F. A., Ramachandar, T., & Liu, H. (2004). Asymmetric synthesis of alpha-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline. Organic Letters, 6(19), 3393-5.
Davis FA, Ramachandar T, Liu H. Asymmetric Synthesis of Alpha-amino 1,3-dithioketals From Sulfinimines (N-sulfinyl Imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline. Org Lett. 2004 Sep 16;6(19):3393-5. PubMed PMID: 15355060.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of alpha-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline. AU - Davis,Franklin A, AU - Ramachandar,Tokala, AU - Liu,Hu, PY - 2004/9/10/pubmed PY - 2005/9/29/medline PY - 2004/9/10/entrez SP - 3393 EP - 5 JF - Organic letters JO - Org Lett VL - 6 IS - 19 N2 - [reaction: see text] N-Sulfinyl alpha-amino 1,3-dithioketals are prepared in high de and good yield by treating sulfinimines with lithio-1,3-dithianes. Selective removal of the N-sulfinyl or the thioketal groups affords stable alpha-amino 1,3-dithioketals and N-sulfinyl alpha-amino ketones, respectively. This new sulfinimine-derived chiral building block is employed in the asymmetric synthesis of polyoxypeptin amino acid (2S,3R)-(-)-3-hydroxy-3-methylproline. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15355060/Asymmetric_synthesis_of_alpha_amino_13_dithioketals_from_sulfinimines__N_sulfinyl_imines___Synthesis_of__2S3R______3_hydroxy_3_methylproline_ DB - PRIME DP - Unbound Medicine ER -