TY - JOUR
T1 - The direct, enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes
T2 - The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions
AU - Hayashi, Yujiro
AU - Urushima, Tatsuya
AU - Shoji, Mitsuru
AU - Uchimaru, Tadafumi
AU - Shiina, Isamu
PY - 2005/10
Y1 - 2005/10
N2 - In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.
AB - In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.
KW - Asymmetric synthesis
KW - Imines
KW - Mannich reaction
KW - Organocatalysis
KW - Proline
UR - http://www.scopus.com/inward/record.url?scp=27544441155&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=27544441155&partnerID=8YFLogxK
U2 - 10.1002/adsc.200505190
DO - 10.1002/adsc.200505190
M3 - Article
AN - SCOPUS:27544441155
SN - 1615-4150
VL - 347
SP - 1595
EP - 1604
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
IS - 11-13
ER -