Title |
Enantiospecific Alkynylation of Alkylboronic Esters
|
---|---|
Published in |
Angewandte Chemie. International Edition, March 2016
|
DOI | 10.1002/anie.201600599 |
Pubmed ID | |
Authors |
Yahui Wang, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal |
Abstract |
Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction. The process involves use of α-lithio vinyl bromide or vinyl carbamate species, for which application to Zweifel-type reactions has not previously been explored. The resulting functionalized 1,1-disubstituted alkenes undergo facile base-mediated elimination to generate terminal alkyne products in high yield and excellent levels of enantiospecificity over a wide range of pinacolboronic ester substrates. Furthermore, along with terminal alkynes, internal and silyl-protected alkynes can be formed by simply introducing a suitable carbon- or silicon-based electrophile after the base-mediated 1,2-elimination reaction. |
X Demographics
Geographical breakdown
Country | Count | As % |
---|---|---|
Germany | 1 | 100% |
Demographic breakdown
Type | Count | As % |
---|---|---|
Scientists | 1 | 100% |
Mendeley readers
Geographical breakdown
Country | Count | As % |
---|---|---|
Japan | 1 | 2% |
Spain | 1 | 2% |
Unknown | 48 | 96% |
Demographic breakdown
Readers by professional status | Count | As % |
---|---|---|
Student > Ph. D. Student | 16 | 32% |
Student > Master | 11 | 22% |
Researcher | 6 | 12% |
Student > Bachelor | 3 | 6% |
Lecturer | 3 | 6% |
Other | 6 | 12% |
Unknown | 5 | 10% |
Readers by discipline | Count | As % |
---|---|---|
Chemistry | 43 | 86% |
Medicine and Dentistry | 1 | 2% |
Design | 1 | 2% |
Unknown | 5 | 10% |