Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.
Catalytic asymmetric conjugate addition reactions with organometallic reagents are powerful reactions in synthetic chemistry. Procedures that use non-stabilized carbanions have been developed extensively, but these suffer from a number of limitations that prevent their use in many situations. Here,...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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2012
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| _version_ | 1797079022248656896 |
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| author | Maksymowicz, R Roth, P Fletcher, S |
| author_facet | Maksymowicz, R Roth, P Fletcher, S |
| author_sort | Maksymowicz, R |
| collection | OXFORD |
| description | Catalytic asymmetric conjugate addition reactions with organometallic reagents are powerful reactions in synthetic chemistry. Procedures that use non-stabilized carbanions have been developed extensively, but these suffer from a number of limitations that prevent their use in many situations. Here, we report that alkylmetal species generated in situ from alkenes can be used in highly enantioselective 1,4-addition initiated by a copper catalyst. Using alkenes as starting materials is desirable because they are readily available and have favourable properties when compared to pre-made organometallics. High levels of enantioselectivity are observed at room temperature in a range of solvents, and the reaction tolerates functional groups that are not compatible with comparable methods-a necessary prerequisite for efficient and protecting-group-free strategies for synthesis. |
| first_indexed | 2024-03-07T00:39:44Z |
| format | Journal article |
| id | oxford-uuid:82a1f12c-6246-4c14-9ff2-cfdad5b53618 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:39:44Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:82a1f12c-6246-4c14-9ff2-cfdad5b536182022-03-26T21:38:46ZCatalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:82a1f12c-6246-4c14-9ff2-cfdad5b53618EnglishSymplectic Elements at Oxford2012Maksymowicz, RRoth, PFletcher, SCatalytic asymmetric conjugate addition reactions with organometallic reagents are powerful reactions in synthetic chemistry. Procedures that use non-stabilized carbanions have been developed extensively, but these suffer from a number of limitations that prevent their use in many situations. Here, we report that alkylmetal species generated in situ from alkenes can be used in highly enantioselective 1,4-addition initiated by a copper catalyst. Using alkenes as starting materials is desirable because they are readily available and have favourable properties when compared to pre-made organometallics. High levels of enantioselectivity are observed at room temperature in a range of solvents, and the reaction tolerates functional groups that are not compatible with comparable methods-a necessary prerequisite for efficient and protecting-group-free strategies for synthesis. |
| spellingShingle | Maksymowicz, R Roth, P Fletcher, S Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents. |
| title | Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents. |
| title_full | Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents. |
| title_fullStr | Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents. |
| title_full_unstemmed | Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents. |
| title_short | Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents. |
| title_sort | catalytic asymmetric carbon carbon bond formation using alkenes as alkylmetal equivalents |
| work_keys_str_mv | AT maksymowiczr catalyticasymmetriccarboncarbonbondformationusingalkenesasalkylmetalequivalents AT rothp catalyticasymmetriccarboncarbonbondformationusingalkenesasalkylmetalequivalents AT fletchers catalyticasymmetriccarboncarbonbondformationusingalkenesasalkylmetalequivalents |