Literature DB >> 15760225

BF3-mediated additions of organolithiums to ketimines: X-ray crystal structures of BF3-ketimine complexes.

Yun Ma1, Emil Lobkovsky, David B Collum.   

Abstract

[reaction: see text] Additions of lithium acetylides and n-BuLi to N-alkyl ketimines mediated by BF(3)-Et(2)O in THF afford hindered tert-alkylamines in moderate to good yields. Stereochemical results and crystal structures of three BF(3)-imine complexes suggest that allylic strain strongly influences conformation and may be an important determinant of reactivity and selectivity.

Entities:  

Mesh：

Substances：

Year:  2005        PMID： 15760225     DOI： 10.1021/jo0480895

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

2.  α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.

Authors:  Anirudra Paul; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

3.  Structures and Reactivities of Sodiated Evans Enolates: Role of Solvation and Mixed Aggregation on the Stereochemistry and Mechanism of Alkylations.

Authors:  Zirong Zhang; David B Collum
Journal:  J Am Chem Soc       Date:  2018-12-17       Impact factor: 15.419

4.  Azaaldol condensation of a lithium enolate solvated by N,N,N',N'-tetramethylethylenediamine: dimer-based 1,2-addition to imines.

Authors:  Timothy S De Vries; Angela M Bruneau; Lara R Liou; Hariharaputhiran Subramanian; David B Collum
Journal:  J Am Chem Soc       Date:  2013-03-04       Impact factor: 15.419

5.  Spectroscopic and X-ray crystallographic evidence for electrostatic effects in 4-substituted cyclohexanone-derived hydrazones, imines, and corresponding salts.

Authors:  David J Dibble; Joseph W Ziller; K A Woerpel
Journal:  J Org Chem       Date:  2011-09-14       Impact factor: 4.354

6.  Evans Enolates: Structures and Mechanisms Underlying the Aldol Addition of Oxazolidinone-Derived Boron Enolates.

Authors:  Zirong Zhang; David B Collum
Journal:  J Org Chem       Date:  2017-07-07       Impact factor: 4.354
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.