Asymmetric carbon-carbon bond formations by conjugate additions of lithiated N-boc allylic amines to nitroalkenes: enantioselective synthesis of functionalized cyclopentanoids.
[reaction: see text] Allylic organolithiums generated by enantioselective deprotonation of N-Boc-N-(p-methoxyphenyl) allylic amines undergo conjugate additions with nitroalkenes to provide enecarbamates containing two contiguous stereogenic centers in good yields with high diastereoselectivities and enantioselectivities. Further elaboration of these adducts to enantioenriched substituted cyclopentanones and aminocyclopentanes is reported.
Johnson
Timothy A
TA
Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 61801, USA.
Curtis
Michael D
MD
Beak
Peter
P
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000588:Amines; D003517:Cyclopentanes; D002244:Carbon; D008094:Lithium