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Five‐Membered Cyclic Nitronates in C–C Coupling with 1‐( tert ‐Butyldimethylsilyloxy)‐1‐methoxyethylene
Author(s) -
Smirnov Vladimir O.,
Sidorenkov Alexander S.,
Khomutova Yulia A.,
Ioffe Sema L.,
Tartakovsky Vladimir A.
Publication year - 2009
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.200900172
Subject(s) - chemistry , ketene , acetal , silylation , methanol , nitroso , medicinal chemistry , coupling (piping) , stereochemistry , organic chemistry , catalysis , mechanical engineering , engineering
Abstract Five‐membered cyclic nitronates 3 undergo TBSOTf‐catalysed C–C coupling reactions with silyl ketene acetal 4 to give good to excellent yields of 3,3‐disubstituted N ‐(OTBS)‐isoxazolidines 5 , which could not be obtained by previously known procedures. The problems of diastereoselectivity of the C–C coupling reactions are discussed. The transformations of the nitroso acetals 5 upon action of Ac F OH/methanol or some reducing agents (H 2 /Ni Ra , LAH, Al/Hg) have been examined.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)