Stereocontrolled Oxidative Additions upon 1,4-Dihydropyridines: Synthesis of Hexahydrofuro[2,3- b ]pyridine and Hexahydropyrano[2,3- b ]pyridine Derivatives.

Autor:	Kumar, Rakesh, Kumar, Dhiraj, Prasad, AshokK.
Předmět:	OXIDATIVE addition DIHYDROPYRIDINE CHEMICAL synthesis PYRIDINE ENAMINES NUCLEOPHILIC reactions RING-opening reactions
Zdroj:	Synthetic Communications; Jan2013, Vol. 43 Issue 4, p520-536, 17p, 5 Diagrams
Abstrakt:	trans-α-Alkoxy-β-halotetrahydropyridines are synthesized in a very efficient single step by stereocontrolled N-halosuccinimide (NXS)–promoted alcohol addition to the enamine group in N-alkyl-1,4-dihydropyridines. These compounds are cyclized using sodium cyanoborohydride in the presence of 2,2′-azobis(2-methylpropionitrile), azabisisobutyronitrile (AIBN) (cat.), and tributylstannane (cat.), affording hexahydrofuro[2,3-b]pyridine and hexahydropyrano[2,3-b]pyridine derivatives. The cyclized product undergoes ring-opening reaction by a nucleophile in the presence of Lewis acid to afford highly functionalized tetrahydropyridines. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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