34
S.C. Pan, B. List
cept in asymmetric catalysis namely ACDC and successfully
applied it to asymmetric iminium catalysis. Asymmetric induction presumably occurs in the cationic iminium ion transition state of the reaction by virtue of a sterochemical communication with the chiral phosphate counteranion, possibly via hydrogen bonding interaction. Our discovery may be of general applicability to other reactions that proceed
via cationic intermediates. Despite its long roots, asymmetric organocatalysis is a relatively new and explosively growing field that, without
doubt, will continue to yield amazing results for some time to come.
Acknowledgements. The present and past co-workers in my laboratory, whose
names are given in the list of references, are highly acknowledged for their hard
work, skill and enthusiasm. I thank the National Institute of Health for funding my work at Scripps. Generous support by the Max-Planck-Society and by
Novartis (Young Investigator Award to BL) is gratefully acknowledged. I also
thank the DFG (Priority Program Organocatalysis SPP1179), Degussa, Wacker,
Merck, Saltigo, Sanofi-Aventis and BASF for general support and donating
chemicals. I also thank Professor Kendall. N. Houk and Professor Walter Thiel
for fruitful collaborations.
References
Agami C (1988) Mechanism of the proline-catalyzed enantioselective aldol reaction. Recent advances. Bull Soc Chim Fr 3:499–507
Agami C, Meynier F, Puchot C, Guilhem J, Pascard C (1984) New insights
into the mechanism of the proline-catalyzed asymmetric Robinson cyclization; structure of two intermediates. Asymmetric dehydration. Tetrahedron
40:1031–1038
Agami C, Puchot C (1986) Kinetic analysis of dual catalysis by proline in an
asymmetric intramolecular aldol reaction. J Mol Catal 38:341–343
Agami C, Puchot C, Sevestre H (1986) Is the mechanism of the proline-catalyzed enantioselective aldol reaction related to biochemical processes?
Tetrahedron Lett 27:1501–1504
Ahrendt KA, Borths CJ, MacMillan DWC (2000) New strategies for organic
catalysis: The first highly enantioselective organocatalytic Diels–Alder reaction. J Am Chem Soc 122:4243–4244
Akiyama T (2004) Preparation of chiral Bronsted catalysts in asym. synthesis and asym. Mannich, aza-Diels–Alder reaction, hydrophosphorylation
therewith. PCT Int Appl WO 200409675, 2004-11-11
S.C. Pan, B. List
cept in asymmetric catalysis namely ACDC and successfully
applied it to asymmetric iminium catalysis. Asymmetric induction presumably occurs in the cationic iminium ion transition state of the reaction by virtue of a sterochemical communication with the chiral phosphate counteranion, possibly via hydrogen bonding interaction. Our discovery may be of general applicability to other reactions that proceed
via cationic intermediates. Despite its long roots, asymmetric organocatalysis is a relatively new and explosively growing field that, without
doubt, will continue to yield amazing results for some time to come.
Acknowledgements. The present and past co-workers in my laboratory, whose
names are given in the list of references, are highly acknowledged for their hard
work, skill and enthusiasm. I thank the National Institute of Health for funding my work at Scripps. Generous support by the Max-Planck-Society and by
Novartis (Young Investigator Award to BL) is gratefully acknowledged. I also
thank the DFG (Priority Program Organocatalysis SPP1179), Degussa, Wacker,
Merck, Saltigo, Sanofi-Aventis and BASF for general support and donating
chemicals. I also thank Professor Kendall. N. Houk and Professor Walter Thiel
for fruitful collaborations.
References
Agami C (1988) Mechanism of the proline-catalyzed enantioselective aldol reaction. Recent advances. Bull Soc Chim Fr 3:499–507
Agami C, Meynier F, Puchot C, Guilhem J, Pascard C (1984) New insights
into the mechanism of the proline-catalyzed asymmetric Robinson cyclization; structure of two intermediates. Asymmetric dehydration. Tetrahedron
40:1031–1038
Agami C, Puchot C (1986) Kinetic analysis of dual catalysis by proline in an
asymmetric intramolecular aldol reaction. J Mol Catal 38:341–343
Agami C, Puchot C, Sevestre H (1986) Is the mechanism of the proline-catalyzed enantioselective aldol reaction related to biochemical processes?
Tetrahedron Lett 27:1501–1504
Ahrendt KA, Borths CJ, MacMillan DWC (2000) New strategies for organic
catalysis: The first highly enantioselective organocatalytic Diels–Alder reaction. J Am Chem Soc 122:4243–4244
Akiyama T (2004) Preparation of chiral Bronsted catalysts in asym. synthesis and asym. Mannich, aza-Diels–Alder reaction, hydrophosphorylation
therewith. PCT Int Appl WO 200409675, 2004-11-11