Direct Carbon− Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters

MC Kohler, JM Yost, MR Garnsey, DM Coltart - Organic letters, 2010 - ACS Publications
An asymmetric Mannich reaction of phenylacetate thioesters and sulfonylimines using
cinchona alkaloid-based amino (thio) urea catalysts is reported that employs proximity …

Enantioselective Mannich reaction of β-keto esters with aromatic and aliphatic imines using a cooperatively assisted bifunctional catalyst

AJ Neuvonen, PM Pihko - Organic letters, 2014 - ACS Publications
An efficient urea-enhanced thiourea catalyst enables the enantioselective Mannich reaction
between β-keto esters and N-Boc-protected imines under mild conditions and minimal …

The mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: Enantioselective synthesis of β-amino acids

J Song, Y Wang, L Deng - Journal of the American Chemical …, 2006 - ACS Publications
We describe the first efficient, direct asymmetric Mannich reactions with malonates and N-
Boc aryl and alkyl imines by cooperative hydrogen-bonding catalysis with a cinchona …

Asymmetric organic catalysis with modified cinchona alkaloids

SK Tian, Y Chen, J Hang, L Tang… - Accounts of chemical …, 2004 - ACS Publications
Insights into the role played by modified cinchona alkaloids in the Sharpless asymmetric
dihydroxylation inspired studies of modified cinchona alkaloids as chiral organic catalysts …

Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis

M Wasa, RY Liu, SP Roche… - Journal of the American …, 2014 - ACS Publications
We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct
reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is …

Cinchona alkaloid-catalyzed asymmetric conjugate additions: the bifunctional Brønsted acid–hydrogen bonding model

MN Grayson, KN Houk - Journal of the American Chemical …, 2016 - ACS Publications
Wynberg's report from 1977 that natural cinchona alkaloids catalyze the asymmetric
conjugate addition of aromatic thiols to cycloalkenones is a landmark discovery in hydrogen …

Organocatalytic enantioselective Mannich reaction: Direct access to chiral β-amino esters

G Ravi Kumar, B Ramesh, S Yarlagadda, B Sridhar… - ACS …, 2019 - ACS Publications
An asymmetric Mannich reaction has been developed to generate chiral β-amino esters in
good yields with excellent enantiomeric excesses (ee, up to 99%) using a chiral bifunctional …

Organocatalytic enantioselective decarboxylative addition of malonic half thioesters to imines

A Ricci, D Pettersen, L Bernardi, F Fini… - Advanced Synthesis …, 2007 - Wiley Online Library
We describe a biomimetic organocatalytic enantioselective decarboxylative addition of
malonic acid half thioesters to imines. This simple protocol makes use of readily available …

Highly Stereoselective, Organocatalytic Mannich-type Addition of Glyoxylate Cyanohydrin: A Versatile Building Block for the Asymmetric Synthesis of β-Amino-α …

Y Tokuhiro, K Yoshikawa, S Murayama, T Nanjo… - ACS …, 2022 - ACS Publications
β-Amino-α-ketoacids are important unnatural amino acids that exhibit unique bioactivity and
reactivity derived from the highly electrophilic carbonyl group at the α-position. Despite the …

Highly regio-, diastereo-, and enantioselective Mannich reaction of allylic ketones and cyclic ketimines: Access to chiral benzosultam

B Qiao, YJ Huang, J Nie, JA Ma - Organic letters, 2015 - ACS Publications
An organocatalytic asymmetric Mannich reaction of allylic ketones with cyclic N-sulfonyl α-
iminoester has been developed. By using a saccharide-derived chiral tertiary amino …