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Origins of opposite absolute stereoselectivities in proline-catalyzed direct Mannich and aldol reactions.
Org Lett. 2003 Apr 17; 5(8):1249-51.OL

Abstract

[structure: see text] The first computational studies to elucidate the stereoselectivity of the proline-catalyzed direct Mannich reaction have been performed using density functional theory (B3LYP/6-31G*). The transition states for the proline-catalyzed direct Mannich reaction of the proline enamine of acetone with the N-phenyl imine of acetaldehyde are reported here. The computed transition states provide a general model that explains the origin of the opposite stereoselectivities of proline-catalyzed Mannich and aldol reactions.

Authors+Show Affiliations

Bahmanyar S
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Houk KN
No affiliation info available

MeSH

AcetaldehydeAldehydesAminesCatalysisIminesMannich BasesModels, ChemicalModels, MolecularProlineStereoisomerism

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12688731

Citation

Bahmanyar, S, and K N. Houk. "Origins of Opposite Absolute Stereoselectivities in Proline-catalyzed Direct Mannich and Aldol Reactions." Organic Letters, vol. 5, no. 8, 2003, pp. 1249-51.
Bahmanyar S, Houk KN. Origins of opposite absolute stereoselectivities in proline-catalyzed direct Mannich and aldol reactions. Org Lett. 2003;5(8):1249-51.
Bahmanyar, S., & Houk, K. N. (2003). Origins of opposite absolute stereoselectivities in proline-catalyzed direct Mannich and aldol reactions. Organic Letters, 5(8), 1249-51.
Bahmanyar S, Houk KN. Origins of Opposite Absolute Stereoselectivities in Proline-catalyzed Direct Mannich and Aldol Reactions. Org Lett. 2003 Apr 17;5(8):1249-51. PubMed PMID: 12688731.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Origins of opposite absolute stereoselectivities in proline-catalyzed direct Mannich and aldol reactions. AU - Bahmanyar,S, AU - Houk,K N, PY - 2003/4/12/pubmed PY - 2003/7/23/medline PY - 2003/4/12/entrez SP - 1249 EP - 51 JF - Organic letters JO - Org Lett VL - 5 IS - 8 N2 - [structure: see text] The first computational studies to elucidate the stereoselectivity of the proline-catalyzed direct Mannich reaction have been performed using density functional theory (B3LYP/6-31G*). The transition states for the proline-catalyzed direct Mannich reaction of the proline enamine of acetone with the N-phenyl imine of acetaldehyde are reported here. The computed transition states provide a general model that explains the origin of the opposite stereoselectivities of proline-catalyzed Mannich and aldol reactions. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12688731/Origins_of_opposite_absolute_stereoselectivities_in_proline_catalyzed_direct_Mannich_and_aldol_reactions_ DB - PRIME DP - Unbound Medicine ER -