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Catalytic enantioselective silylation of N-sulfonylimines: asymmetric synthesis of α-amino acids from CO2 via stereospecific carboxylation of α-amino silanes.
Org Lett. 2014 Jun 06; 16(11):3028-31.OL

Abstract

A catalytic enantioselective silylation of N-tert-butylsulfonylimines using a Cu-secondary diamine complex was demonstrated. The resulting optically active α-amino silanes could be carboxylated under a CO2 atmosphere (1 atm) to afford the corresponding α-amino acids in a stereoretentive manner. This two-step sequence provides a new synthetic protocol for optically active α-amino acids from gaseous CO2 and imines in the presence of a catalytic amount of a chiral source.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Mita T
Faculty of Pharmaceutical Sciences, Hokkaido University , Sapporo 060-0812, Japan.
Sugawara M
No affiliation info available
Saito K
No affiliation info available
Sato Y
No affiliation info available

MeSH

Amino AcidsCarboxylic AcidsCatalysisDiaminesIminesMolecular StructureSilanesStereoisomerismSulfones

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24834796

Citation

Mita, Tsuyoshi, et al. "Catalytic Enantioselective Silylation of N-sulfonylimines: Asymmetric Synthesis of Α-amino Acids From CO2 Via Stereospecific Carboxylation of Α-amino Silanes." Organic Letters, vol. 16, no. 11, 2014, pp. 3028-31.
Mita T, Sugawara M, Saito K, et al. Catalytic enantioselective silylation of N-sulfonylimines: asymmetric synthesis of α-amino acids from CO2 via stereospecific carboxylation of α-amino silanes. Org Lett. 2014;16(11):3028-31.
Mita, T., Sugawara, M., Saito, K., & Sato, Y. (2014). Catalytic enantioselective silylation of N-sulfonylimines: asymmetric synthesis of α-amino acids from CO2 via stereospecific carboxylation of α-amino silanes. Organic Letters, 16(11), 3028-31. https://doi.org/10.1021/ol501143c
Mita T, et al. Catalytic Enantioselective Silylation of N-sulfonylimines: Asymmetric Synthesis of Α-amino Acids From CO2 Via Stereospecific Carboxylation of Α-amino Silanes. Org Lett. 2014 Jun 6;16(11):3028-31. PubMed PMID: 24834796.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective silylation of N-sulfonylimines: asymmetric synthesis of α-amino acids from CO2 via stereospecific carboxylation of α-amino silanes. AU - Mita,Tsuyoshi, AU - Sugawara,Masumi, AU - Saito,Keisuke, AU - Sato,Yoshihiro, Y1 - 2014/05/16/ PY - 2014/5/20/entrez PY - 2014/5/20/pubmed PY - 2014/10/7/medline SP - 3028 EP - 31 JF - Organic letters JO - Org Lett VL - 16 IS - 11 N2 - A catalytic enantioselective silylation of N-tert-butylsulfonylimines using a Cu-secondary diamine complex was demonstrated. The resulting optically active α-amino silanes could be carboxylated under a CO2 atmosphere (1 atm) to afford the corresponding α-amino acids in a stereoretentive manner. This two-step sequence provides a new synthetic protocol for optically active α-amino acids from gaseous CO2 and imines in the presence of a catalytic amount of a chiral source. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24834796/Catalytic_enantioselective_silylation_of_N_sulfonylimines:_asymmetric_synthesis_of_α_amino_acids_from_CO2_via_stereospecific_carboxylation_of_α_amino_silanes_ DB - PRIME DP - Unbound Medicine ER -