Amino acid mediated intramolecular asymmetric aldol reaction to construct a new chiral bicyclic enedione containing a seven-membered ring: remarkable inversion of enantioselectivity compared to the six-membered ring example

Takashi Nagamine; Kohei Inomata; Yasuyuki Endo; Leo A Paquette

doi:10.1021/jo061824n

Amino acid mediated intramolecular asymmetric aldol reaction to construct a new chiral bicyclic enedione containing a seven-membered ring: remarkable inversion of enantioselectivity compared to the six-membered ring example

J Org Chem. 2007 Jan 5;72(1):123-31. doi: 10.1021/jo061824n.

Authors

Takashi Nagamine¹, Kohei Inomata, Yasuyuki Endo, Leo A Paquette

Affiliation

¹ Tohoku Pharmaceutical University, 4-4-1 Komatsushima Aoba-ku, Sendai 981-8558 Japan.

PMID: 17194090
DOI: 10.1021/jo061824n

Abstract

A detailed study to assess the enantioselectivity of the amino acid mediated intramolecular asymmetric aldol reaction of 1,3-cycloheptanedione bearing a C-2 methyl substituent has been undertaken. The cyclizations were mediated by a series of l-amino acids in the presence of an acid cocatalyst. Strikingly, the process is characterized by an inversion of enantioselectivity when compared to a similar reaction involving the 1,3-cyclohexanedione counterpart.

MeSH terms

Amino Acids / chemistry*
Bridged Bicyclo Compounds / chemistry*
Catalysis
Molecular Structure
Solvents
Stereoisomerism

Substances

Amino Acids
Bridged Bicyclo Compounds
Solvents