Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine

Tetrahedron ◽  
2012 ◽  
Vol 68 (22) ◽  
pp. 4302-4319 ◽  
Author(s):  
Stephen G. Davies ◽  
James A. Lee ◽  
Paul M. Roberts ◽  
James E. Thomson ◽  
Callum J. West
Keyword(s):  
Asymmetric Synthesis ◽  
Homoallylic Amines

scholarly journals A One-Pot Asymmetric Synthesis of Homoallylic Amines via Indium-Mediated Allylation of Hydrazones

2013 ◽  
Vol 34 (11) ◽  
pp. 3193-3194 ◽  
Author(s):  
Jun Hyuk Lee ◽  
Tae Kyu Nam ◽  
Apuri Satyender ◽  
Doo Ok Jang
Keyword(s):  
Asymmetric Synthesis ◽  
One Pot ◽  
Homoallylic Amines

Asymmetric synthesis with the robust and versatile 10-substituted 9-borabicyclo[3.3.2]decanes: Homoallylic amines from aldimines

2006 ◽  
Vol 78 (7) ◽  
pp. 1389-1395 ◽  
Author(s):  
Eliud Hernandez ◽  
Eda Canales ◽  
Eduvigis Gonzalez ◽  
John A. Soderquist
Keyword(s):  
Asymmetric Synthesis ◽  
New Method ◽  
Homoallylic Amines ◽  
Work Up

The asymmetric allylboration of N-H aldimines, generated from either N-trimethylsilyl or N-diisobutylalanyl precursors, with B-allyl-9-borabicyclo[3.3.2]decane is described. The desired homoallylic amines are obtained efficiently (60-90 %) and selectively (60-89 % ee). A non-oxidative work-up procedure has also been developed for this new method, which permits the recovery of the air-stable pseudoephedrine (PE) complex (50-70 %), which is conveniently converted back to B-allyl-9-borabicyclo[3.3.2]decane (98 %) with allylmagnesium bromide in ether for its reuse in the asymmetric allylboration process. Additional studies were conducted to better understand these processes and the origin of the observed enantioselectivity.

Asymmetric synthesis of homoallylic amines via 1,2-addition of Grignard reagent to aliphatic N-phosphonyl hemiaminal

2016 ◽  
Vol 57 (5) ◽  
pp. 619-622 ◽  
Author(s):  
Shuo Qiao ◽  
Suresh Pindi ◽  
Preston T. Spigener ◽  
Bo Jiang ◽  
Guigen Li
Keyword(s):  
Asymmetric Synthesis ◽  
Grignard Reagent ◽  
Homoallylic Amines
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