Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives.

Autor:	Yang SM; Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C., Madhusudhan Reddy G; Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C., Liu MH; Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C., Wang TP; Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C., Yu JK; Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C., Lin W; Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2017 Jan 06; Vol. 82 (1), pp. 781-789. Date of Electronic Publication: 2016 Dec 12.
DOI:	10.1021/acs.joc.6b02526
Abstrakt:	A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.
Databáze:	MEDLINE
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