Abstract
Catalytic enantioselective methodology has dramatically been enriched by the re-discovery of the simple amino acid proline as a chiral catalyst in the year 2000. Although no catalyst offers such a simple and broad access to quite complex reaction products, as does proline, its synthetic potential is not unrestricted, what is especially connected to its poor solubility in organic media. Exchange of the carboxylic moiety by a tetrazole unit leads to proline surrogates, that by far outperform proline with respect to yield, enantioselectivity, reaction time, substrate and solvent scope, catalyst loading, and stoichiometry of the compounds used in excess. These factors are discussed and critically compared with selected representative proline-catalyzed reactions.
TY - JOUR
T1 - 5-(pyrrolidin-2-yl)-1H-tetrazole and 5-[(pyrrolidin-2-yl)methyl]-1H-tetrazole: proline surrogates with increased potential in asymmetric catalysis.
A1 - Limbach,Michael,
PY - 2006/12/29/pubmed
PY - 2007/3/21/medline
PY - 2006/12/29/entrez
SP - 119
EP - 33
JF - Chemistry & biodiversity
JO - Chem Biodivers
VL - 3
IS - 2
N2 - Catalytic enantioselective methodology has dramatically been enriched by the re-discovery of the simple amino acid proline as a chiral catalyst in the year 2000. Although no catalyst offers such a simple and broad access to quite complex reaction products, as does proline, its synthetic potential is not unrestricted, what is especially connected to its poor solubility in organic media. Exchange of the carboxylic moiety by a tetrazole unit leads to proline surrogates, that by far outperform proline with respect to yield, enantioselectivity, reaction time, substrate and solvent scope, catalyst loading, and stoichiometry of the compounds used in excess. These factors are discussed and critically compared with selected representative proline-catalyzed reactions.
SN - 1612-1880
UR - https://www.unboundmedicine.com/medline/citation/17193251/5__pyrrolidin_2_yl__1H_tetrazole_and_5_[_pyrrolidin_2_yl_methyl]_1H_tetrazole:_proline_surrogates_with_increased_potential_in_asymmetric_catalysis_
L2 - https://doi.org/10.1002/cbdv.200690016
DB - PRIME
DP - Unbound Medicine
ER -
