Journal
ORGANIC LETTERS
Volume 21, Issue 8, Pages 2509-2513Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b04110
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Funding
- SERB, India [EMR/2014/000207]
- IIT Gandhinagar
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The first vinylogous aldol condensation of alpha,beta-unsaturated aldehydes using aqueous formaldehyde is developed under mild reaction conditions to form the gamma-methylenated products with excellent regioselectivity. Using this methodology, a short synthesis of alpha-triticene, an antifungal compound, is achieved in two steps. The practicality of this methodology is demonstrated by the gram-scale synthesis. Formation of the unusual double gamma-functionalized products from crotonaldehyde and a direct asymmetric vinylogous aldol product from phenylglyoxal is also described.
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