Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins

Organic Letters

Volumn 9, Issue 4, 2007, Pages 599-602

  McCooey, Séamus H ^a   Connon, Stephen J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847793920     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0628006     Document Type: Article

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73. As this manuscript was being reviewed, a report appeared online detailing the use of 9-epi-DHQA as an organocatayst for promotion of Michael addition reactions via "iminium ion" catalysis: Xie, J.-W.; Chen,. W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2006, 45, early view.
74. See Supporting Information for details.
75. Only Tsogoeva (91% ee, ref 7a) and Jacobsen (99% ee, ref 7b) have reported amine-based catalysts capable of promoting this reaction with >55% ee.
76. Tsogoeva (ref 7a) and Jacobsen (ref 7b) have recently reported bifunctional thiourea-based catalysts that promote highly enantioselective reactions with this substrate class with anti diastereoselectivity.
77. For discussion, see ref 5e and references therein.
78. Polymerization was the major fate of the nitroolefin substrate in the absence of a Brønsted acid co-catalyst.