Synthesis of 3-Pyrrolines, Annulated 3-Pyrrolines, and Pyrroles from α-Amino Allenes
摘要:
[GRAPHICS]alpha -Amino allenes, readily prepared from reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates followed by N-Boc deprotection, are converted in high yields to pyrrolines with AgNO3. Palladium-catalyzed cyclization of amino allenes affords either the pyrroline or the pyrrole depending on reaction conditions and provides for introduction of an aryl substituent at the C-3 position of the pyrroline or pyrrole. Enantioenriched pyrrolines are readily prepared from scalemic propargyl alcohols.
Study of the regiochemistry and stereochemistry of the [3 + 2] cycloaddition between nonstabilized azomethine ylides generated from tertiary amine N-oxides and various dipolarophiles
作者:Jacqueline Chastanet、Georges Roussi
DOI:10.1021/jo00251a026
日期:1988.8
CHASTANET, JACQUELINE;ROUSSI, GEORGES, J. ORG. CHEM., 53,(1988) N 16, C. 3808-3812