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Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.14/1168584
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- Title
- Enantioselective Trifunctional Organocatalysts for Rate-Enhanced Aza-Morita-Baylis-Hillman Reactions at Room Temperature
- Related
- Advanced Synthesis and Catalysis, Vol. 351, No. 3, (2009), p.331-338
- DOI
- 10.1002/adsc.200800679
- Publisher
- Wiley-VCH Verlag GmbH & Co. KGaA
- Date
- 2009
- Author/Creator
- Garnier, Jean-Marc Daniel
- Author/Creator
- Anstiss, Christopher Luke
- Author/Creator
- Liu, Fei
- Description
- A Brønsted acid-activated trifunctional organocatalyst, based on the BINAP scaffold, was used for the first time to catalyze aza-Morita-Baylis- Hillman reactions between N-tosylimines and methyl vinyl ketone with fast reaction rates and good enantioselectivity at room temperature. This trifunctional catalyst, containing a Lewis base, a Brønsted base, and a Brønsted acid, required acid activation to confer its enantioselectivity and rate improvement for both electron-rich and electrondeficient imine substrates. The role of the amino Lewis base of la was investigated and found to be the activity switch in response to an acid additive. The counterion of the acid additive was found to influence not only the excess ratio but also the sense of asymmetric induction.
- Description
- 8 page(s)
- Subject Keyword
- 030500 Organic Chemistry
- Subject Keyword
- Asymmetric catalysis
- Subject Keyword
- Aza-Morita-Baylis-Hillman reaction
- Subject Keyword
- Chiral amine protonation
- Subject Keyword
- Cooperative effects
- Subject Keyword
- Ion pairs
- Resource Type
- journal article
- Organisation
- Macquarie University. Department of Chemistry and Biomolecular Sciences
- Identifier
- http://hdl.handle.net/1959.14/1168584
- Identifier
- mq:58123
- Identifier
- ISSN:1615-4150
- Identifier
- mq-rm-2008002446
- Language
- eng
- Reviewed
Macquarie University ResearchOnline
