Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones.
We report theoretical studies into the remote 1,5-stereoinduction shown by certain types of beta-alkoxy methyl ketones in boron-mediated aldol reactions with achiral aldehydes. For a range of common alkoxy groups, our calculations are in excellent agreement with experimentally observed diastereosele...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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2006
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| _version_ | 1797058868988084224 |
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| author | Paton, R Goodman, J |
| author_facet | Paton, R Goodman, J |
| author_sort | Paton, R |
| collection | OXFORD |
| description | We report theoretical studies into the remote 1,5-stereoinduction shown by certain types of beta-alkoxy methyl ketones in boron-mediated aldol reactions with achiral aldehydes. For a range of common alkoxy groups, our calculations are in excellent agreement with experimentally observed diastereoselectivities. In the aldol transition structures, a stabilizing hydrogen bond between the alkoxy oxygen and formyl proton leads to preferential formation of the 1,5-adduct, by minimizing steric interactions between the beta-alkyl group and one of the ligands on boron. |
| first_indexed | 2024-03-06T19:56:27Z |
| format | Journal article |
| id | oxford-uuid:25c3eb8b-2a19-4c86-8fee-f173fefec211 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:56:27Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:25c3eb8b-2a19-4c86-8fee-f173fefec2112022-03-26T11:57:22ZUnderstanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:25c3eb8b-2a19-4c86-8fee-f173fefec211EnglishSymplectic Elements at Oxford2006Paton, RGoodman, JWe report theoretical studies into the remote 1,5-stereoinduction shown by certain types of beta-alkoxy methyl ketones in boron-mediated aldol reactions with achiral aldehydes. For a range of common alkoxy groups, our calculations are in excellent agreement with experimentally observed diastereoselectivities. In the aldol transition structures, a stabilizing hydrogen bond between the alkoxy oxygen and formyl proton leads to preferential formation of the 1,5-adduct, by minimizing steric interactions between the beta-alkyl group and one of the ligands on boron. |
| spellingShingle | Paton, R Goodman, J Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones. |
| title | Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones. |
| title_full | Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones. |
| title_fullStr | Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones. |
| title_full_unstemmed | Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones. |
| title_short | Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones. |
| title_sort | understanding the origins of remote asymmetric induction in the boron aldol reactions of beta alkoxy methyl ketones |
| work_keys_str_mv | AT patonr understandingtheoriginsofremoteasymmetricinductionintheboronaldolreactionsofbetaalkoxymethylketones AT goodmanj understandingtheoriginsofremoteasymmetricinductionintheboronaldolreactionsofbetaalkoxymethylketones |