Stereoelectronic effect for the selectivity in C-H insertion of alkylidene carbenes and its application to the synthesis of platensimycin.
A systematic study of C-H insertion reactions with variously substituted and conformationally constrained substrates was carried out. High selectivity in the insertion between two competing C-H bonds caused by a strong stereoelectronic effect of an oxygen substituent was achieved. This regioselective C-H insertion reaction was employed as a platform to develop a concise asymmetric synthesis of platensimycin.
Yun
Sang Young
SY
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Zheng
Jun-Cheng
JC
Lee
Daesung
D
D000218:Adamantane / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D062365:Aminobenzoates / Q000138:chemical synthesis*; D000813:Anilides / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D062365:Aminobenzoates; D000813:Anilides; D004987:Ethers; D007659:Ketones; C030011:carbene; D008697:Methane; D000218:Adamantane; C510909:platensimycin