A Recyclable Organocascade Reaction System: Stereoselective Precipitation of Optically Active cis-δ-Lactols with Quaternary Stereocenters during the Michael-Hemiacetalization Reaction
A cascade Michael–hemiacetalization reaction between β‐substituted β‐nitroethanols and α,β‐unsaturated aldehydes is described, which provides a convenient and efficient synthesis for cis‐δ‐lactols with quaternary stereocenters in moderate yields with excellent enantioselectivity. Based on the select...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2010-11, Vol.352 (17), p.2875-2880 |
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| container_issue | 17 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 352 |
| creator | Zhang, Fanglin Wei, Mohui Dong, Junfang Zhou, Yirong Lu, Dengfu Gong, Yuefa Yang, Xiangliang |
| description | A cascade Michael–hemiacetalization reaction between β‐substituted β‐nitroethanols and α,β‐unsaturated aldehydes is described, which provides a convenient and efficient synthesis for cis‐δ‐lactols with quaternary stereocenters in moderate yields with excellent enantioselectivity. Based on the selective precipitation of cis‐δ‐lactols, which were isolated by filtration, the catalytic system in the filtrate can be reused directly and recycled for eight times without any obvious deterioration in enantioselectivity. |
| doi_str_mv | 10.1002/adsc.201000553 |
| format | Article |
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Based on the selective precipitation of cis‐δ‐lactols, which were isolated by filtration, the catalytic system in the filtrate can be reused directly and recycled for eight times without any obvious deterioration in enantioselectivity.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201000553</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>cascade reaction ; green chemistry ; hydrogen bonding ; organocatalysis ; quaternary stereocenters</subject><ispartof>Advanced synthesis & catalysis, 2010-11, Vol.352 (17), p.2875-2880</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. 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Based on the selective precipitation of cis‐δ‐lactols, which were isolated by filtration, the catalytic system in the filtrate can be reused directly and recycled for eight times without any obvious deterioration in enantioselectivity.</description><subject>cascade reaction</subject><subject>green chemistry</subject><subject>hydrogen bonding</subject><subject>organocatalysis</subject><subject>quaternary stereocenters</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkMFS2zAURT2dMtM0dNu1fsCpZFl21F0m0ISZQKBJ6VLzIj8nAsXOSA5gvotFv6LfhMCQ6a6rd0e65743N4q-MjpglCbfoPB6kNCgqRD8Q9RjGRNxyjL58aAF_RR99v6GUpYP87wX_RmRn6hbbWFlkczdGqpag9dQYPgA3Zi6IovWN7j9ThYNOqw9Wgzvd0guHWqzMw28uuqSzHeN0WBtS0adQxsf_32KZyGotp7cm2ZDrvYQcipw7VugxipMT4q9M9WaNBsk50ZvAG08xa0BjQ1Y89hteT_qODoqwXr88jb70a8fp8vxNJ7NJ2fj0SzWPMl5PAQhIKUso4VMNaMlFbIcsixP5bCANBGQYcqTJIG0gJXkhSxzSUvgKyEYZZz3o0GXq13tvcNS7ZzZhuMVo-qld_XSuzr0HgDZAffGYvsftxqdLMb_snHHmlD4w4EFd6uynOdC_b6YKDmZXS-XQVzzZ274m6s</recordid><startdate>20101122</startdate><enddate>20101122</enddate><creator>Zhang, Fanglin</creator><creator>Wei, Mohui</creator><creator>Dong, Junfang</creator><creator>Zhou, Yirong</creator><creator>Lu, Dengfu</creator><creator>Gong, Yuefa</creator><creator>Yang, Xiangliang</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20101122</creationdate><title>A Recyclable Organocascade Reaction System: Stereoselective Precipitation of Optically Active cis-δ-Lactols with Quaternary Stereocenters during the Michael-Hemiacetalization Reaction</title><author>Zhang, Fanglin ; Wei, Mohui ; Dong, Junfang ; Zhou, Yirong ; Lu, Dengfu ; Gong, Yuefa ; Yang, Xiangliang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3273-8a55a40160d94c10f059f8167498da425a6e43222a4dab93d9f790fa3b5510133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>cascade reaction</topic><topic>green chemistry</topic><topic>hydrogen bonding</topic><topic>organocatalysis</topic><topic>quaternary stereocenters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Fanglin</creatorcontrib><creatorcontrib>Wei, Mohui</creatorcontrib><creatorcontrib>Dong, Junfang</creatorcontrib><creatorcontrib>Zhou, Yirong</creatorcontrib><creatorcontrib>Lu, Dengfu</creatorcontrib><creatorcontrib>Gong, Yuefa</creatorcontrib><creatorcontrib>Yang, Xiangliang</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Fanglin</au><au>Wei, Mohui</au><au>Dong, Junfang</au><au>Zhou, Yirong</au><au>Lu, Dengfu</au><au>Gong, Yuefa</au><au>Yang, Xiangliang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Recyclable Organocascade Reaction System: Stereoselective Precipitation of Optically Active cis-δ-Lactols with Quaternary Stereocenters during the Michael-Hemiacetalization Reaction</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2010-11-22</date><risdate>2010</risdate><volume>352</volume><issue>17</issue><spage>2875</spage><epage>2880</epage><pages>2875-2880</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A cascade Michael–hemiacetalization reaction between β‐substituted β‐nitroethanols and α,β‐unsaturated aldehydes is described, which provides a convenient and efficient synthesis for cis‐δ‐lactols with quaternary stereocenters in moderate yields with excellent enantioselectivity. Based on the selective precipitation of cis‐δ‐lactols, which were isolated by filtration, the catalytic system in the filtrate can be reused directly and recycled for eight times without any obvious deterioration in enantioselectivity.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201000553</doi><tpages>6</tpages></addata></record> |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | cascade reaction green chemistry hydrogen bonding organocatalysis quaternary stereocenters |
| title | A Recyclable Organocascade Reaction System: Stereoselective Precipitation of Optically Active cis-δ-Lactols with Quaternary Stereocenters during the Michael-Hemiacetalization Reaction |
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