Asymmetric synthesis of 4,5,6- and 3,4,5,6-substituted azepanes by a highly diastereoselective and enantioselective lithiation-conjugate addition sequence.
Asymmetric syntheses of 4,5,6- and 3,4,5,6-substituted azepanes have been achieved by highly diastereoselective and enantioselective (-)-sparteine-mediated asymmetric lithiation-conjugate additions of N-Boc-N-(p-methoxyphenyl)-2,3-substituted allylamines to a beta-aryl alpha,beta-unsaturated ester followed by hydrolysis, cyclization, and reduction. Access to the enantiomeric adduct is provided by an invertive lithiation-stannylation-lithiation sequence.
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.
Suk Joong
SJ
Lee
Peter
P
Beak
D000499:Allylamine / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry; D003500:Cyclization; D008094:Lithium / Q000737:chemistry*; D013034:Sparteine / Q000737:chemistry; D013237:Stereoisomerism
D001381:Azepines; D001596:Benzylamines; C029991:N-methylbenzylamine; D013034:Sparteine; D000499:Allylamine; D008094:Lithium