Spiro-Pyrrolidine-Catalyzed Asymmetric Conjugate Addition of Hydroxylamine to Enals and 2,4-Dienals

被引：37

作者：

Dou, Qing-Yun ^{[1
,2
,3
]}

Tu, Yong-Qiang ^{[1
,2
,3
]}

Zhang, Ye ^{[1
,2
,3
]}

Tian, Jin-Miao ^{[1
,2
,3
]}

Zhang, Fu-Min ^{[1
,2
,3
]}

Wang, Shao-Hua ^{[1
,2
,3
,4
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China

[4] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 06期

关键词：

asymmetric catalysis; aza-1,4-addition; aza-1,6-addition; spiro-pyrrolidines; PHOSPHONATED CARBOCYCLIC 2'-OXA-3'-AZANUCLEOSIDES; DIELS-ALDER REACTIONS; MICHAEL ADDITION; SEMIPINACOL REARRANGEMENT; HIGHLY REGIO; ALDEHYDES; ORGANOCATALYSTS; 1,6-ADDITIONS; EFFICIENT; CASCADE;

D O I：

10.1002/adsc.201501025

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页码：874 / 879

页数：6

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