Spiro‐Pyrrolidine‐Catalyzed Asymmetric Conjugate Addition of Hydroxylamine to Enals and 2,4‐Dienals | Zendy

Dou QingYun | Zendy; Tu YongQiang | Zendy; Zhang Ye | Zendy; Tian JinMiao | Zendy; Zhang FuMin | Zendy; Wang ShaoHua | Zendy

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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.

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