Tags

Type your tag names separated by a space and hit enter

Expedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions.
Org Lett. 2006 Jun 22; 8(13):2839-42.OL

Abstract

[reaction: see text] Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamines from phthalimido ketones.

Authors+Show Affiliations

Chowdari NS
The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
Ahmad M
No affiliation info available
Albertshofer K
No affiliation info available
Tanaka F
No affiliation info available
Barbas CF
No affiliation info available

MeSH

AzidesCatalysisDiaminesIminesKetonesMolecular StructureProlineStereoisomerismTetrazoles

Pub Type(s)

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

Language

eng

PubMed ID

16774270

Citation

Chowdari, Naidu S., et al. "Expedient Synthesis of Chiral 1,2- and 1,4-diamines: Protecting Group Dependent Regioselectivity in Direct Organocatalytic Asymmetric Mannich Reactions." Organic Letters, vol. 8, no. 13, 2006, pp. 2839-42.
Chowdari NS, Ahmad M, Albertshofer K, et al. Expedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions. Org Lett. 2006;8(13):2839-42.
Chowdari, N. S., Ahmad, M., Albertshofer, K., Tanaka, F., & Barbas, C. F. (2006). Expedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions. Organic Letters, 8(13), 2839-42.
Chowdari NS, et al. Expedient Synthesis of Chiral 1,2- and 1,4-diamines: Protecting Group Dependent Regioselectivity in Direct Organocatalytic Asymmetric Mannich Reactions. Org Lett. 2006 Jun 22;8(13):2839-42. PubMed PMID: 16774270.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Expedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions. AU - Chowdari,Naidu S, AU - Ahmad,Moballigh, AU - Albertshofer,Klaus, AU - Tanaka,Fujie, AU - Barbas,Carlos F,3rd PY - 2006/6/16/pubmed PY - 2007/4/17/medline PY - 2006/6/16/entrez SP - 2839 EP - 42 JF - Organic letters JO - Org Lett VL - 8 IS - 13 N2 - [reaction: see text] Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamines from phthalimido ketones. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16774270/Expedient_synthesis_of_chiral_12__and_14_diamines:_protecting_group_dependent_regioselectivity_in_direct_organocatalytic_asymmetric_Mannich_reactions_ DB - PRIME DP - Unbound Medicine ER -