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Nickel‐Catalyzed Annulation of Donor–Acceptor Oxiranes with Imines: Diastereoselective Access to Highly Substituted 2,4‐ trans ‐Oxazolidines
Author(s) -
Zhang Junqing,
Xiao Yuanjing,
Zhang Junliang
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300449
Subject(s) - chemistry , annulation , catalysis , cycloaddition , nickel , cleavage (geology) , medicinal chemistry , bond cleavage , ring (chemistry) , acceptor , stereochemistry , photochemistry , combinatorial chemistry , organic chemistry , physics , geotechnical engineering , fracture (geology) , engineering , condensed matter physics
An efficient approach for the synthesis of highly substituted 2,4‐ trans ‐oxazolidines has been achieved by means of nickel(II) chlorate hexahydrate [Ni(ClO 4 ) 2 ⋅6 H 2 O]‐catalyzed [3+2] dipolar cycloaddition reactions of donor–acceptor oxiranes with imines via CC bond cleavage in good yields with moderate to high diastereoselectivity. The appropriate orientation of two activating ketones or esters is crucial for this chemoselective CC bond cleavage of the oxirane ring.