Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds
Abstract Allylic alcohols were found to undergo a semipinacol-type rearrangement induced by halogen cation generated from the chloramine-T/ZnX 2 combination, which provided a highly efficient and stereoselective method for the preparation of α-quaternary β-haloketo compounds. This reaction is valuab...
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| Veröffentlicht in: | Synlett 2003-08, Vol.2003 (10) |
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| container_title | Synlett |
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| creator | Wang, Bao Min Song, Zhen Lei Fan, Chun An Tu, Yong Qiang Chen, Wei Ming |
| description | Abstract
Allylic alcohols were found to undergo a semipinacol-type rearrangement
induced by halogen cation generated from the chloramine-T/ZnX
2
combination,
which provided a highly efficient and stereoselective method for
the preparation of α-quaternary β-haloketo compounds.
This reaction is valuable and versatile since a quaternary carbon
could be constructed effectively and three kinds of β-haloketo
compounds (X = Cl, Br, I) could be achieved
readily. |
| doi_str_mv | 10.1055/s-2003-40855 |
| format | Article |
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Allylic alcohols were found to undergo a semipinacol-type rearrangement
induced by halogen cation generated from the chloramine-T/ZnX
2
combination,
which provided a highly efficient and stereoselective method for
the preparation of α-quaternary β-haloketo compounds.
This reaction is valuable and versatile since a quaternary carbon
could be constructed effectively and three kinds of β-haloketo
compounds (X = Cl, Br, I) could be achieved
readily.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-2003-40855</identifier><language>eng</language><subject>letter</subject><ispartof>Synlett, 2003-08, Vol.2003 (10)</ispartof><rights>Georg Thieme Verlag Stuttgart ˙ New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2003-40855.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2003-40855$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Wang, Bao Min</creatorcontrib><creatorcontrib>Song, Zhen Lei</creatorcontrib><creatorcontrib>Fan, Chun An</creatorcontrib><creatorcontrib>Tu, Yong Qiang</creatorcontrib><creatorcontrib>Chen, Wei Ming</creatorcontrib><title>Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds</title><title>Synlett</title><addtitle>Synlett</addtitle><description>Abstract
Allylic alcohols were found to undergo a semipinacol-type rearrangement
induced by halogen cation generated from the chloramine-T/ZnX
2
combination,
which provided a highly efficient and stereoselective method for
the preparation of α-quaternary β-haloketo compounds.
This reaction is valuable and versatile since a quaternary carbon
could be constructed effectively and three kinds of β-haloketo
compounds (X = Cl, Br, I) could be achieved
readily.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNotkFFKxDAQhoMouK6-eYC8SzRtktr4Voq6Cwuiq88lTdJt1mxSmqzQw3gIPcieyVaFgR_-GWb--QC4TPB1ghm7CSjFmCCKc8aOwCyh5HZ0eHYMZpiTDLE0oafgLIQtxgnNOZ6Bz4WwfqMdLEU03sGlU3upFVxH3WsftNUymg8N13pnOuOE9BbFodPwRYu-F26jd9pF6BtYWDtYI0eVvvU23MECLsymtQO8bxojzTRXdF3vhWxh9PDwhZ73YrzjRD_AwzeaorzrsVP6Xef3ToVzcNIIG_TFv87B28P9a7lAq6fHZVmsUEhyHhFVpG4kpTVWohEsJ0ryFOs8wVTUWGimUip41pCMcZmPZpYRruhYOeE4q8kcXP3tja0ZH6q2fj-msqFKcDWRrUI1ka1-yZIf3uRwJw</recordid><startdate>20030805</startdate><enddate>20030805</enddate><creator>Wang, Bao Min</creator><creator>Song, Zhen Lei</creator><creator>Fan, Chun An</creator><creator>Tu, Yong Qiang</creator><creator>Chen, Wei Ming</creator><scope/></search><sort><creationdate>20030805</creationdate><title>Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds</title><author>Wang, Bao Min ; Song, Zhen Lei ; Fan, Chun An ; Tu, Yong Qiang ; Chen, Wei Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-s189t-4d3bfc44b0dafa583dc920e8104ab0ae5d24a96f3659c804a6639d49d483906b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Bao Min</creatorcontrib><creatorcontrib>Song, Zhen Lei</creatorcontrib><creatorcontrib>Fan, Chun An</creatorcontrib><creatorcontrib>Tu, Yong Qiang</creatorcontrib><creatorcontrib>Chen, Wei Ming</creatorcontrib><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Bao Min</au><au>Song, Zhen Lei</au><au>Fan, Chun An</au><au>Tu, Yong Qiang</au><au>Chen, Wei Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2003-08-05</date><risdate>2003</risdate><volume>2003</volume><issue>10</issue><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>Abstract
Allylic alcohols were found to undergo a semipinacol-type rearrangement
induced by halogen cation generated from the chloramine-T/ZnX
2
combination,
which provided a highly efficient and stereoselective method for
the preparation of α-quaternary β-haloketo compounds.
This reaction is valuable and versatile since a quaternary carbon
could be constructed effectively and three kinds of β-haloketo
compounds (X = Cl, Br, I) could be achieved
readily.</abstract><doi>10.1055/s-2003-40855</doi></addata></record> |
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| issn | 0936-5214 1437-2096 |
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| source | Thieme Connect Journals |
| subjects | letter |
| title | Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds |
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