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One‐Pot Stereoselective Synthesis of ( Z )‐β‐Ketoenamides from β‐Halo α,β‐Unsaturated Aldehydes
Author(s) -
Gogoi Junali,
Gogoi Pranjal,
Boruah Romesh C.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400007
Subject(s) - chemistry , halo , stereoselectivity , formylation , derivative (finance) , aldehyde , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , physics , quantum mechanics , galaxy , financial economics , economics
A series of steroidal and non‐steroidal β‐ketoenamides have been synthesized from their corresponding β‐halo α,β‐unsaturated aldehydes. This synthetic methodology provides efficient access to ( Z )‐β‐ketoenamides. The structures of these products have been unambiguously established by single crystal XRD studies. This process is found to be mild and inexpensive. The required β‐halo α,β‐unsaturated aldehydes are synthesized from corresponding ketones using the Vilsmeier formylation reaction. One of the prepared β‐ketoenamides was transformed into its corresponding 2‐aminodihydroisoquinoline derivative.