Stereospecific Ring Contraction of Bromocycloheptenes through Dyotropic Rearrangements via Nonclassical Carbocation–Anion Pairs
Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calcu...
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| Published in | Journal of the American Chemical Society Vol. 140; no. 15; pp. 4986 - 4990 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
18.04.2018
American Chemical Society (ACS) Amer Chemical Soc |
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| ISSN | 0002-7863 1520-5126 1520-5126 |
| DOI | 10.1021/jacs.8b00821 |
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| Abstract | Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calculations show that the reaction proceeds through a nonclassical carbocation–anion pair, which is crucial for the low activation barrier and enantiospecificity. The chiral cyclopropylcarbinyl cation may be a transition state or an intermediate, depending on the reaction conditions. |
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| AbstractList | Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calculations show that the reaction proceeds through a nonclassical carbocation-anion pair, which is crucial for the low activation barrier and enantiospecificity. The chiral cyclopropylcarbinyl cation may be a transition state or an intermediate, depending on the reaction conditions. Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calculations show that the reaction proceeds through a nonclassical carbocation–anion pair, which is crucial for the low activation barrier and enantiospecificity. The chiral cyclopropylcarbinyl cation may be a transition state or an intermediate, depending on the reaction conditions. Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calculations show that the reaction proceeds through a nonclassical carbocation–anion pair, which is crucial for the low activation barrier and enantiospecificity. The chiral cyclopropylcarbinyl cation may be a transition state or an intermediate, depending on the reaction conditions. Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calculations show that the reaction proceeds through a nonclassical carbocation-anion pair, which is crucial for the low activation barrier and enantiospecificity. The chiral cyclopropylcarbinyl cation may be a transition state or an intermediate, depending on the reaction conditions.Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and stereospecific ring contraction of bromocycloheptenes. This reaction occurs under mild conditions, with or without a Lewis acid catalyst. DFT calculations show that the reaction proceeds through a nonclassical carbocation-anion pair, which is crucial for the low activation barrier and enantiospecificity. The chiral cyclopropylcarbinyl cation may be a transition state or an intermediate, depending on the reaction conditions. |
| Author | Houk, K. N Fujita, Makoto Feringa, Ben L Guduguntla, Sureshbabu Kikuchi, Takashi Goh, Shermin S Champagne, Pier Alexandre |
| AuthorAffiliation | University of Groningen University of CaliforniaLos Angeles Department of Applied Chemistry University of Tokyo Stratingh Institute for Chemistry Department of Chemistry and Biochemistry Rigaku Corporation |
| AuthorAffiliation_xml | – name: University of Tokyo – name: University of CaliforniaLos Angeles – name: Department of Applied Chemistry – name: Rigaku Corporation – name: Stratingh Institute for Chemistry – name: University of Groningen – name: Department of Chemistry and Biochemistry |
| Author_xml | – sequence: 1 givenname: Shermin S surname: Goh fullname: Goh, Shermin S organization: University of Groningen – sequence: 2 givenname: Pier Alexandre orcidid: 0000-0002-0546-7537 surname: Champagne fullname: Champagne, Pier Alexandre organization: University of CaliforniaLos Angeles – sequence: 3 givenname: Sureshbabu surname: Guduguntla fullname: Guduguntla, Sureshbabu organization: University of Groningen – sequence: 4 givenname: Takashi surname: Kikuchi fullname: Kikuchi, Takashi organization: Rigaku Corporation – sequence: 5 givenname: Makoto orcidid: 0000-0001-6105-7340 surname: Fujita fullname: Fujita, Makoto organization: University of Tokyo – sequence: 6 givenname: K. N orcidid: 0000-0002-8387-5261 surname: Houk fullname: Houk, K. N email: houk@chem.ucla.edu organization: University of CaliforniaLos Angeles – sequence: 7 givenname: Ben L orcidid: 0000-0003-0588-8435 surname: Feringa fullname: Feringa, Ben L email: b.l.feringa@rug.nl organization: University of Groningen |
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| Keywords | CYCLOBUTYL SYMMETRY CONTROLLED REACTIONS ENANTIOSELECTIVE SYNTHESIS BETA-LACTONES ALLYLIC ALKYLATION INTERCONVERSION REACTIONS CYCLOPROPYLCARBINYL DISCOVERY CONJUGATE ADDITION BUTYROLACTONES |
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| Snippet | Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and... Experimental and theoretical evidence is reported for a rare type I dyotropic rearrangement involving a [1,2]-alkene shift, leading to the regio- and... |
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| SubjectTerms | ALLYLCARBINYL DERIVATIVES ALLYLIC SUBSTITUTION-REACTIONS BETA-LACTONES BUTYROLACTONES catalysts cations Chemical Sciences Chemistry Chemistry, Multidisciplinary Communication CONJUGATE ADDITION CYCLOPROPYLCARBINYL ENANTIOSELECTIVE SYNTHESIS General Chemistry GRIGNARD-REAGENTS INTERCONVERSION REACTIONS Lewis acids Physical Sciences Science & Technology SYMMETRY CONTROLLED REACTIONS |
| Title | Stereospecific Ring Contraction of Bromocycloheptenes through Dyotropic Rearrangements via Nonclassical Carbocation–Anion Pairs |
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