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Spiro‐Pyrrolidine‐Catalyzed Asymmetric Conjugate Addition of Hydroxylamine to Enals and 2,4‐Dienals
Author(s) -
Dou QingYun,
Tu YongQiang,
Zhang Ye,
Tian JinMiao,
Zhang FuMin,
Wang ShaoHua
Publication year - 2016
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.201501025
Subject(s) - pyrrolidine , chemistry , hydroxylamine , conjugate , catalysis , tandem , organic chemistry , medicinal chemistry , mathematical analysis , materials science , mathematics , composite material
A spiro‐pyrrolidine‐catalyzed tandem aza‐1,4‐addition/hemi‐acetalization reaction was developed with excellent enantioselectivity (12 examples of ≥99% ee ), and several substrates proceeded with higher ee (up to 10% increase) compared with the literature data. Particularly, an interesting and unusual aza‐1,6‐/oxa‐1,4‐addition for some substrates was also observed.