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Stereoselective Amine Addition to Six‐Membered Cyclic Nitronates Promoted by Silyl Triflate
Author(s) -
Mikhaylov Andrey A.,
Dilman Alexander D.,
Khomutova Yulia A.,
Arkhipov Dmitry E.,
Korlyukov Alexander A.,
Ioffe Sema L.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300511
Subject(s) - chemistry , silylation , trifluoromethanesulfonate , nitroso , electrophile , stereoselectivity , nitro , amine gas treating , medicinal chemistry , yield (engineering) , catalysis , organic chemistry , alkyl , materials science , metallurgy
Six‐membered cyclic nitronates couple with amines or their N ‐silyl derivatives in a diastereoselective fashion to give 3‐amino‐substituted nitroso acetals in 53–89 % yield through silyl triflate electrophilic catalysis. Stereodifferentiation of this process is determined by thermodynamic control, which is realized due to reversibility of amine addition and a decreased nitrogen inversion barrier in the resulting nitroso acetals. Selected chemical transformations of nitroso acetals were examined.