Rhodium-Catalyzed Asymmetric Intramolecular Cyclopropanation of Substituted Allylic Cyanodiazoacetates
A chiral rhodium catalyst, Rh2[4S‐(4′)‐FBNAZ]4, was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. Alkenes bearing an electron‐deficient substituent including carbonyl and halogens are converted into the corresponding cyclopropane...
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| Published in | Advanced synthesis & catalysis Vol. 347; no. 11-13; pp. 1547 - 1552 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.10.2005
WILEY‐VCH Verlag Wiley |
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| Abstract | A chiral rhodium catalyst, Rh2[4S‐(4′)‐FBNAZ]4, was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. Alkenes bearing an electron‐deficient substituent including carbonyl and halogens are converted into the corresponding cyclopropanes in high yields with both chiral and achiral rhodium catalysts. The cyclopropane derivatives were generated with an enantioselectivity of up to 91% ee. For the asymmetric intramolecular cyclopropanation, cis‐halogen‐substituted substrates afforded cyclopropanes with higher enantioselectivities than the corresponding trans diastereomers. However, only moderate enantioselectivities were observed with alkenes bearing electron‐donating groups such as alkyls. The cyclopropanation of 3‐substituted 2‐propenyl cyanodiazoacetates was strongly influenced by steric and electronic factors arising from substituents on the alkenes. For the first time, we demonstrated that the intramolecular reaction of gem‐dihaloallylic cyanodiazoacetate afforded highly functionalized gem‐dihalocyclopropanes. This reaction is an appealing alternative to the addition of dihalocarbenes to alkenes for the formation of gem‐dihalocyclopropanes. |
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| AbstractList | A chiral rhodium catalyst, Rh2[4S‐(4′)‐FBNAZ]4, was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. Alkenes bearing an electron‐deficient substituent including carbonyl and halogens are converted into the corresponding cyclopropanes in high yields with both chiral and achiral rhodium catalysts. The cyclopropane derivatives were generated with an enantioselectivity of up to 91% ee. For the asymmetric intramolecular cyclopropanation, cis‐halogen‐substituted substrates afforded cyclopropanes with higher enantioselectivities than the corresponding trans diastereomers. However, only moderate enantioselectivities were observed with alkenes bearing electron‐donating groups such as alkyls. The cyclopropanation of 3‐substituted 2‐propenyl cyanodiazoacetates was strongly influenced by steric and electronic factors arising from substituents on the alkenes. For the first time, we demonstrated that the intramolecular reaction of gem‐dihaloallylic cyanodiazoacetate afforded highly functionalized gem‐dihalocyclopropanes. This reaction is an appealing alternative to the addition of dihalocarbenes to alkenes for the formation of gem‐dihalocyclopropanes. A chiral rhodium catalyst, Rh-2[4S-(4')FBNAZ](4), was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. Alkenes bearing an electron-deficient substituent including carbonyl and halogens are converted into the corresponding cyclopropanes in high yields with both chiral and achiral rhodium catalysts. The cyclopropane derivatives were generated with an enantioselectivity of up to 91% ee. For the asymmetric intramolecular cyclopropanation, cis-halogen-substituted substrates afforded cyclopropanes with higher enantioselectivities than the corresponding trans diastereomers. However, only moderate enantioselectivities were observed with alkenes bearing electron -donating groups such as alkyls. The cyclopropanation of 3-substituted 2-propenyl cyanodiazoacetates was strongly influenced by steric and electronic factors arising from substituents on the alkenes. For the first time, we demonstrated that the intramolecular reaction of gem-dihaloallylic cyanodiazoacetate afforded highly functionalized gem-dihalocyclopropanes. This reaction is an appealing alternative to the addition of dihalocarbenes to alkenes for the formation of gem-dihalocyclopropanes. A chiral rhodium catalyst, Rh 2 [4 S ‐(4′)‐FBNAZ] 4 , was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. Alkenes bearing an electron‐deficient substituent including carbonyl and halogens are converted into the corresponding cyclopropanes in high yields with both chiral and achiral rhodium catalysts. The cyclopropane derivatives were generated with an enantioselectivity of up to 91% ee. For the asymmetric intramolecular cyclopropanation, cis ‐halogen‐substituted substrates afforded cyclopropanes with higher enantioselectivities than the corresponding trans diastereomers. However, only moderate enantioselectivities were observed with alkenes bearing electron‐donating groups such as alkyls. The cyclopropanation of 3‐substituted 2‐propenyl cyanodiazoacetates was strongly influenced by steric and electronic factors arising from substituents on the alkenes. For the first time, we demonstrated that the intramolecular reaction of gem ‐dihaloallylic cyanodiazoacetate afforded highly functionalized gem ‐dihalocyclopropanes. This reaction is an appealing alternative to the addition of dihalocarbenes to alkenes for the formation of gem ‐dihalocyclopropanes. |
| Author | Charette, André B. Lin, Wei |
| Author_xml | – sequence: 1 givenname: Wei surname: Lin fullname: Lin, Wei organization: Département de Chimie, Université de Montréal, P. O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada, Phone: (+1)-514-343-2432, Fax: (+1)-514-343-5900 – sequence: 2 givenname: André B. surname: Charette fullname: Charette, André B. email: andre.charette@umontreal.ca organization: Département de Chimie, Université de Montréal, P. O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada, Phone: (+1)-514-343-2432, Fax: (+1)-514-343-5900 |
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| Copyright | Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | DIAZOACETATES ALPHA-DIAZO CARBONYL DIRHODIUM(II) AMINO-ACIDS cyanodiazoacetates halocyclopropanes BETA-KETO SULFONES PHENYLALANINE chiral catalyst intramolecular cyclopropanation PHENYLIODONIUM YLIDES rhodium |
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| Snippet | A chiral rhodium catalyst, Rh2[4S‐(4′)‐FBNAZ]4, was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic... A chiral rhodium catalyst, Rh-2[4S-(4')FBNAZ](4), was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic... A chiral rhodium catalyst, Rh 2 [4 S ‐(4′)‐FBNAZ] 4 , was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic... |
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| SubjectTerms | Chemistry Chemistry, Applied Chemistry, Organic chiral catalyst cyanodiazoacetates halocyclopropanes intramolecular cyclopropanation Physical Sciences rhodium Science & Technology |
| Title | Rhodium-Catalyzed Asymmetric Intramolecular Cyclopropanation of Substituted Allylic Cyanodiazoacetates |
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