Regioselectivity of alkylidene carbene-mediated C-H insertion was explored utilizing electronic, conformational, steric, and stereoelectronic effects. Relying on these factors, highly regio- and chemoselective carbene insertion reaction of C-H bonds in different environments could be obtained. The observed selectivity clearly indicates that an electronic effect plays a more important role than steric effect.
View Article and Find Full Text PDFA 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.
View Article and Find Full Text PDF[reaction: see text] Optically active cis-2-substituted vinylaziridines are synthesized by the reaction of N-tert-butylsulfinylimines with telluronium ylides with excellent diastereoselectivity in good to excellent yields.
View Article and Find Full Text PDFThe Michael addition-elimination of ylide to alpha,beta-unsaturated imines leads to a highly diastereoselective and enantioselective synthesis of vinylcyclopropanecarbaldehydes in good to high yields for the first time. A sequential cyclopropanation-aziridination protocol for the preparation of cyclopropylaziridines is also developed with good diastereoselectivity in good to high yields.
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