The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles.
The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized alpha- and beta-amino acids, beta-lactams, and amino alcohols.
Notz
Wolfgang
W
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Tanaka
Fujie
F
Watanabe
Shin-Ichi
S
Chowdari
Naidu S
NS
Turner
James M
JM
Thayumanavan
Rajeswari
R
Barbas
Carlos F
CF
D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes; D007097:Imines / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry*; D008956:Models, Chemical; D011392:Proline / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000447:Aldehydes; D000596:Amino Acids; D000605:Amino Alcohols; D004146:Dioxanes; D007097:Imines; D007769:Lactams; D008352:Mannich Bases; D011759:Pyrrolidines; D012997:Solvents; D011392:Proline