Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate. A Novel Asymmetric Synthesis of Unsaturated Aromatic 1,2-Amino Alcohols

The diastereoselective synthesis of unsaturated aromatic 1,2-amino alcohols can be achieved on an epimeric mixture of optically active allylic ethers having a hydroxyl group attached to an allylic chiral center to the π-system using chlorosulfonyl isocyanate. These reactions produced the unsaturated...

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Veröffentlicht in:	Journal of organic chemistry 2003-05, Vol.68 (9), p.3721-3724
Hauptverfasser:	Kim, Ji Duck, Zee, Ok Pyo, Jung, Young Hoon
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Sprache:	eng
Schlagworte:	Aliphatic compounds Chemistry Exact sciences and technology Organic chemistry Preparations and properties
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container_title	Journal of organic chemistry
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description	The diastereoselective synthesis of unsaturated aromatic 1,2-amino alcohols can be achieved on an epimeric mixture of optically active allylic ethers having a hydroxyl group attached to an allylic chiral center to the π-system using chlorosulfonyl isocyanate. These reactions produced the unsaturated anti-1,2-amino alcohols either exclusively or predominantly only for aromatic derivatives. The anti-selectivity may be explained by the Cieplak electronic model during the conversion from ethers to carbamates.
doi_str_mv	10.1021/jo0267089
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The anti-selectivity may be explained by the Cieplak electronic model during the conversion from ethers to carbamates.</description><subject>Aliphatic compounds</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNptkc1u1DAUhSMEokNhwQsgb6hUiRT_xLGzjIYWikaAaIdZWh7PTcfFsYudVORteFRczajDgruxdP35nOt7iuI1wWcEU_L-NmBaCyybJ8WMcIrLusHV02KGMaUlozU7Kl6kdItzcc6fF0eECsKYlLPiz3e4sSGBAzPYe0Dab9AHq9MAEf5pt85NzhrU9tbrwQaPlsn6GzTfuhBDGl0X_OTQZQpm0pmAM9SiL-EeHGrT1PcwxPz6avLDFpJNKHRo6ZMexpjZDWpj6LOsQeQdLR88QnY0YRtcelk867RL8Gp_HhfLi_Pr-ady8fXj5bxdlJqJZiiFpHhNORfEMGhAAJYdJrLhsm4MwTVmkhla8w3oCqThwI3Ra6g4yKqjDWPHxclO9y6GXyOkQfU2GXBOewhjUoJRXknMM3i6A03-eIrQqbtoex0nRbB6iEM9xpHZN3vRcd3D5kDu95-Bt3tAJ6NdF7U3Nh24SlQM4zpz5Y6zOZnfj_c6_lS1YIKr629Xiv5YXawWn1dqddDVJuV5xujz7v4z4F_oAq92</recordid><startdate>20030502</startdate><enddate>20030502</enddate><creator>Kim, Ji Duck</creator><creator>Zee, Ok Pyo</creator><creator>Jung, Young Hoon</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20030502</creationdate><title>Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate. 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subjects	Aliphatic compounds Chemistry Exact sciences and technology Organic chemistry Preparations and properties
title	Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate. A Novel Asymmetric Synthesis of Unsaturated Aromatic 1,2-Amino Alcohols
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