Abstract
Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including α-allenyl ketones and amino-substituted heterocycles.
| Original language | English |
|---|---|
| Pages (from-to) | 195-202 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 136 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 8 Jan 2014 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes. / Chuprakov, Stepan; Worrell, Brady T.; Selander, Nicklas; Sit, Rakesh K.; Fokin, Valery V.
In: Journal of the American Chemical Society, Vol. 136, No. 1, 08.01.2014, p. 195-202.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes
AU - Chuprakov, Stepan
AU - Worrell, Brady T.
AU - Selander, Nicklas
AU - Sit, Rakesh K.
AU - Fokin, Valery V.
PY - 2014/1/8
Y1 - 2014/1/8
N2 - Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including α-allenyl ketones and amino-substituted heterocycles.
AB - Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including α-allenyl ketones and amino-substituted heterocycles.
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UR - http://www.scopus.com/inward/citedby.url?scp=84892181640&partnerID=8YFLogxK
U2 - 10.1021/ja408185c
DO - 10.1021/ja408185c
M3 - Article
VL - 136
SP - 195
EP - 202
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 1
ER -