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1. Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl Amides

Author:
Borhan, Babak,   et al.   ; Soltanzadeh, Bardia; Jaganathan, Arvind; Yi, Yi; Yi, Hajoon; Staples, Richard J.;     Show all 6 Authors
Source:
Journal of the American Chemical Society 2017 v.139 no.6 pp. 2132-2135
ISSN:
1520-5126
Subject:
amides; catalysts; enantiomers; salts
Abstract:
... We report a highly regio-, diastereo- and enantioselective vicinal dihalogenation of allyl amides. E- and Z-alkenes with both aryl and alkyl substituents were compatible with this chemistry. This is the result of exquisite catalyst controlled regioselectivity enabling use of electronically unbiased substrates. The reaction employs commercially available catalysts and halenium sources along with ch ...
DOI:
10.1021/jacs.6b09203

2. A New Tool To Guide Halofunctionalization Reactions: The Halenium Affinity (HalA) Scale

Author:
Borhan, Babak,   et al.   ; Ashtekar, Kumar Dilip; Marzijarani, Nastaran Salehi; Jaganathan, Arvind; Holmes, Daniel; Jackson, James E.;     Show all 6 Authors
Source:
Journal of the American Chemical Society 2014 v.136 no.38 pp. 13355-13362
ISSN:
1520-5126
Subject:
alkenes; amides; amines; chemical reactions; ions; oxygen; prediction
Abstract:
... We introduce a previously unexplored parameterhalenium affinity (HalA)– as a quantitative descriptor of the bond strengths of various functional groups to halenium ions. The HalA scale ranks potential halenium ion acceptors based on their ability to stabilize a “free halenium ion”. Alkenes in particular but other Lewis bases as well, such as amines, amides, carbonyls, and ether oxygen atoms, etc. ...
DOI:
10.1021/ja506889c

3. Chlorosulfonamide Salts Are Superior Electrophilic Chlorine Precursors for the Organocatalytic Asymmetric Chlorocyclization of Unsaturated Amides

Author:
Borhan, Babak,   et al.   ; Jaganathan, Arvind;     Show all 2 Author
Source:
Organic letters 2014 v.16 no.14 pp. 3616-3619
ISSN:
1523-7052
Subject:
Lewis acids; alkenes; ambient temperature; amides; catalytic activity; chemical reactions; chemical structure; chlorine; salts; stereoselectivity
Abstract:
... Chloramine-T·3H₂O and other chlorosulfonamide salts can serve as readily available, stable, and inexpensive precursors of electrophilic chlorine in the organocatalytic asymmetric chlorofunctionalization of olefins. In conjunction with commercially available organocatalysts, they can be utilized in the asymmetric chlorocyclization of unsaturated amides to yield products with unprecedented levels of ...
DOI:
10.1021/ol500861z

4. Kinetic Resolution of Unsaturated Amides in a Chlorocyclization Reaction: Concomitant Enantiomer Differentiation and Face Selective Alkene Chlorination by a Single Catalyst

Author:
Borhan, Babak,   et al.   ; Jaganathan, Arvind; Staples, Richard J.;     Show all 3 Authors
Source:
Journal of the American Chemical Society 2013 v.135 no.39 pp. 14806-14813
ISSN:
1520-5126
Subject:
amides; catalysts; chlorination; chlorine; enantiomers; hydrogen bonding; olefin; solvents; stereoisomerism
Abstract:
... The first example of a kinetic resolution via chlorofunctionalization of olefins is reported. The enantiomers of racemic unsaturated amides were found to have different hydrogen-bonding affinities for chiral Lewis bases in numerous solvents. This interaction was exploited in developing a kinetic resolution of racemic unsaturated amides via halocyclization. The same catalyst serves to both “sense c ...
DOI:
10.1021/ja407241d