Oxazaborolidines as Functional Monomers: Ketone Reduction Using Polymer-Supported Corey, Bakshi, and Shibata Catalysts
The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in t...
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| Veröffentlicht in: | Journal of organic chemistry 2002-11, Vol.67 (23), p.8086-8089 |
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| container_end_page | 8089 |
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| container_issue | 23 |
| container_start_page | 8086 |
| container_title | Journal of organic chemistry |
| container_volume | 67 |
| creator | Price, Michael D Sui, Jennifer K Kurth, Mark J Schore, Neil E |
| description | The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model. |
| doi_str_mv | 10.1021/jo026132n |
| format | Article |
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Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo026132n</identifier><identifier>PMID: 12423136</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.</description><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Price, Michael D</creatorcontrib><creatorcontrib>Sui, Jennifer K</creatorcontrib><creatorcontrib>Kurth, Mark J</creatorcontrib><creatorcontrib>Schore, Neil E</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Price, Michael D</au><au>Sui, Jennifer K</au><au>Kurth, Mark J</au><au>Schore, Neil E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxazaborolidines as Functional Monomers: Ketone Reduction Using Polymer-Supported Corey, Bakshi, and Shibata Catalysts</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-11-15</date><risdate>2002</risdate><volume>67</volume><issue>23</issue><spage>8086</spage><epage>8089</epage><pages>8086-8089</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. 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| source | ACS Publications |
| subjects | Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Oxazaborolidines as Functional Monomers: Ketone Reduction Using Polymer-Supported Corey, Bakshi, and Shibata Catalysts |
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