Highly Enantioselective Synthesis of (S)-α-Alkyl-α,β-diaminopropionic Acids via Asymmetric Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-imidazoline-4-carboxylic Acid tert-Butyl Esters
An efficient enantioselective synthetic method for (S)-α-alkyl-α,β-diaminopropionic acid is reported. The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the correspondin...
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| Veröffentlicht in: | Organic letters 2009-08, Vol.11 (16), p.3738-3741 |
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| container_end_page | 3741 |
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| container_issue | 16 |
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| container_title | Organic letters |
| container_volume | 11 |
| creator | Park, Yohan Kang, Sukhoon Lee, Young Ju Kim, Taek-Soo Jeong, Byeong-Seon Park, Hyeung-geun Jew, Sang-sup |
| description | An efficient enantioselective synthetic method for (S)-α-alkyl-α,β-diaminopropionic acid is reported. The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the corresponding alkylated products (93−98% ee) which could be transformed to enantioenriched α-alkyl-α,β-diaminopropionic acids. |
| doi_str_mv | 10.1021/ol9013552 |
| format | Article |
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The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the corresponding alkylated products (93−98% ee) which could be transformed to enantioenriched α-alkyl-α,β-diaminopropionic acids.</description><subject>Alkylation</subject><subject>beta-Alanine - analogs & derivatives</subject><subject>beta-Alanine - chemical synthesis</subject><subject>beta-Alanine - chemistry</subject><subject>Catalysis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9uEzEQhy0EoiVw4AWQLyAqYVh7197sMUSBIlWiUst5NWtPiIvXDrZTsbwVvABv0GfCUaJy4TR_9OkbjX6EPOfVW14J_i64ruK1lOIBOeVS1KytpHh436vqhDxJ6aaqeNl0j8kJ71TdzLvqlPw5t183bqIrDz7bkNChzvYW6dXk8waTTTSs6eurM3b3iy3ct8mV5s3db2YsjNaHbQxbG7zVdKGtSfTWAl2kaRwxx7K83EBCdh3BpzVGuoQMbsp7eq-CctHv_YJdbtAXt2B2tAZ-Bmc9soZpiEP4Mbmjn2aMmb3f5cnRVSpDekoercElfHasM_Llw-p6ec4uPn_8tFxcMKh5nVkjBjlX2jRzxA6kVnM1gJGmRiE7WSNHo4bOtI3WphUtN1y3jRr4YEAo1UA9I68O3vLw9x2m3I82aXQOPIZd6lWrhGxLCjNydgB1DClFXPfbaEeIU8-rfp9Wf59WYV8cpbthRPOPPMZTgJcHAHTqb8Iu-vLjf0R_Aa1poOg</recordid><startdate>20090820</startdate><enddate>20090820</enddate><creator>Park, Yohan</creator><creator>Kang, Sukhoon</creator><creator>Lee, Young Ju</creator><creator>Kim, Taek-Soo</creator><creator>Jeong, Byeong-Seon</creator><creator>Park, Hyeung-geun</creator><creator>Jew, Sang-sup</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090820</creationdate><title>Highly Enantioselective Synthesis of (S)-α-Alkyl-α,β-diaminopropionic Acids via Asymmetric Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-imidazoline-4-carboxylic Acid tert-Butyl Esters</title><author>Park, Yohan ; Kang, Sukhoon ; Lee, Young Ju ; Kim, Taek-Soo ; Jeong, Byeong-Seon ; Park, Hyeung-geun ; Jew, Sang-sup</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-42b586cd48ee9a5c686bad5d3e25953e1ed6b9d74ccd7271d1c746b1bda2664a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkylation</topic><topic>beta-Alanine - analogs & derivatives</topic><topic>beta-Alanine - chemical synthesis</topic><topic>beta-Alanine - chemistry</topic><topic>Catalysis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Yohan</creatorcontrib><creatorcontrib>Kang, Sukhoon</creatorcontrib><creatorcontrib>Lee, Young Ju</creatorcontrib><creatorcontrib>Kim, Taek-Soo</creatorcontrib><creatorcontrib>Jeong, Byeong-Seon</creatorcontrib><creatorcontrib>Park, Hyeung-geun</creatorcontrib><creatorcontrib>Jew, Sang-sup</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Park, Yohan</au><au>Kang, Sukhoon</au><au>Lee, Young Ju</au><au>Kim, Taek-Soo</au><au>Jeong, Byeong-Seon</au><au>Park, Hyeung-geun</au><au>Jew, Sang-sup</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Enantioselective Synthesis of (S)-α-Alkyl-α,β-diaminopropionic Acids via Asymmetric Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-imidazoline-4-carboxylic Acid tert-Butyl Esters</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2009-08-20</date><risdate>2009</risdate><volume>11</volume><issue>16</issue><spage>3738</spage><epage>3741</epage><pages>3738-3741</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An efficient enantioselective synthetic method for (S)-α-alkyl-α,β-diaminopropionic acid is reported. The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the corresponding alkylated products (93−98% ee) which could be transformed to enantioenriched α-alkyl-α,β-diaminopropionic acids.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19634890</pmid><doi>10.1021/ol9013552</doi><tpages>4</tpages></addata></record> |
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| ispartof | Organic letters, 2009-08, Vol.11 (16), p.3738-3741 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkylation beta-Alanine - analogs & derivatives beta-Alanine - chemical synthesis beta-Alanine - chemistry Catalysis Combinatorial Chemistry Techniques Molecular Structure Stereoisomerism |
| title | Highly Enantioselective Synthesis of (S)-α-Alkyl-α,β-diaminopropionic Acids via Asymmetric Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-imidazoline-4-carboxylic Acid tert-Butyl Esters |
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