Synthesis of vinylcyclopropanes from epoxides
Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropan...
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| Published in | Journal of organic chemistry Vol. 56; no. 2; pp. 717 - 723 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.01.1991
Amer Chemical Soc |
| Subjects | |
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| Abstract | Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an S(Ni) process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinylcyclopropanes with functionality on the olefin. |
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| AbstractList | Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an S(Ni) process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinylcyclopropanes with functionality on the olefin. |
| Author | Kirschning, Andreas Narjes, Frank Schaumann, Ernst |
| Author_xml | – sequence: 1 givenname: Ernst surname: Schaumann fullname: Schaumann, Ernst – sequence: 2 givenname: Andreas surname: Kirschning fullname: Kirschning, Andreas – sequence: 3 givenname: Frank surname: Narjes fullname: Narjes, Frank |
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| Keywords | ORGANIC-SYNTHESIS 1,3-DIENES OXIRANES AMBIENT-TEMPERATURE SUBSTITUTED VINYLCYCLOPROPANES GENERATION VINYL-CYCLOPROPANES ELECTROPHILES STEREOSELECTIVE SYNTHESIS CYCLO-ADDITION |
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REACTIONS OF OMEGA-BROMOALKYL P-TOLYL SULPHONES WITH BASES- ROLE OF INDUCTIVE EFFECTS IN ELIMINATION AND SUBSTITUTION publication-title: JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC contributor: fullname: KNIPE, AC – volume: 39 start-page: 2323 year: 1983 ident: WOS:A1983RA40900001 article-title: RECENT ADVANCES IN THE PREPARATION AND SYNTHETIC APPLICATIONS OF OXIRANES publication-title: TETRAHEDRON contributor: fullname: RAO, AS – volume: 29 start-page: 4281 year: 1988 ident: WOS:A1988P818800019 article-title: RING-OPENING OF OXIRANES BY SILYL-SUBSTITUTED ALLYL ANIONS - A REGIOCHEMICAL CHAMELEON publication-title: TETRAHEDRON LETTERS contributor: fullname: SCHAUMANN, E – volume: 48 start-page: 34 year: 1983 ident: WOS:A1983PY52600007 article-title: A SYNTHESIS OF 3-BETA-HYDROXY-5-BETA, 14-ALPHA-BUFA-20,22-DIENOLIDE FROM DEOXYCORTICOSTERONE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BAUER, PE |
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| Snippet | Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or... |
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| SubjectTerms | Chemistry Chemistry, Organic Exact sciences and technology Organic chemistry Physical Sciences Science & Technology |
| Title | Synthesis of vinylcyclopropanes from epoxides |
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