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Synlett 2014; 25(1): 143-147 DOI: 10.1055/s-0033-1340077 Asymmetric Synthesis of Oxa-spirocyclic Indanones with Structural Com-plexity via an Organocatalytic Michael¨CHenry¨CAcetalization Cascade Xin Xie, Cheng Peng*a, b, Hai-Jun Lengb, Biao Wangb, Zheng-Wei Tanga, Wei Huang*a |
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- LS-EPI: 1647
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- ÔÚÏß: 13328.4Сʱ
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Èë²ØºÅ: WOS:000328606500024 Asymmetric Synthesis of Oxa-spirocyclic Indanones with Structural Complexity via an Organocatalytic Michael-Henry-Acetalization Cascade ×÷Õß:Xie, X (Xie, Xin)[ 1 ] ; Peng, C (Peng, Cheng)[ 1,2 ] ; Leng, HJ (Leng, Hai-Jun)[ 2 ] ; Wang, B (Wang, Biao)[ 2 ] ; Tang, ZW (Tang, Zheng-Wei)[ 1 ] ; Huang, W (Huang, Wei)[ 1 ] SYNLETT ¾í: 25 ÆÚ: 1 Ò³: 143-147 DOI: 10.1055/s-0033-1340077 ³ö°æÄê: JAN 2 2014 ²é¿´ÆÚ¿¯ÐÅÏ¢ ÕªÒª The highly enantioselective preparation of drug-like oxa-spirocyclic indanone derivatives employing a multicomponent cascade reaction is described. This approach utilizes an organocatalytic Michael reaction followed by a Henry-acetalization sequence that yields the desired chiral spirocyclic backbone, bearing four contiguous stereogenic centers and multiple functional groups, in good yields and high stereoselectivities (up to 99% ee and 95:5 dr). ¹Ø¼ü´Ê ×÷Õ߹ؼü´Ê rganocatalysis; chiral indanone; oxa-spirocycles; tandem reactions; asymmetric synthesisKeyWords Plus IPHENYLPROLINOL SILYL ETHER; RECEPTOR ANTAGONISTS; 4 STEREOCENTERS; EFFICIENT; ADDITIONS; NITROALKENES; DERIVATIVES; ACTIVATION; CATALYSIS; ALDEHYDES×÷ÕßÐÅÏ¢ ͨѶ×÷ÕßµØÖ·: Peng, C (ͨѶ×÷Õß) Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Peoples R China. µØÖ·: [ 1 ] Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Peoples R China [ 2 ] Chengdu Univ Tradit Chinese Med, Sch Pharm, Chengdu 611137, Peoples R China µç×ÓÓʼþµØÖ·:pengchengchengdu@126.com; huangwei@cdutcm.edu.cn »ù½ð×ÊÖúÖÂл »ù½ð×ÊÖú»ú¹¹ ÊÚȨºÅ Specialized Research Fund for the Doctoral Program of Higher Education 20125132120005 Application Foundation of the Science and Technology Department of Sichuan Province 2011JZY037 National Science Foundation of China 81303208 ²é¿´»ù½ð×ÊÖúÐÅÏ¢ ³ö°æÉÌ GEORG THIEME VERLAG KG, RUDIGERSTR 14, D-70469 STUTTGART, GERMANY Àà±ð / ·ÖÀà Ñо¿·½Ïò:Chemistry Web of Science Àà±ð:Chemistry, Organic ÎÄÏ×ÐÅÏ¢ ÎÄÏ×ÀàÐÍ:Article ÓïÖÖ:English Èë²ØºÅ: WOS:000328606500024 ISSN: 0936-5214 µç×Ó ISSN: 1437-2096 ÆÚ¿¯ÐÅÏ¢ Impact Factor (Ó°ÏìÒò×Ó): Journal Citation Reports® ÆäËûÐÅÏ¢ IDS ºÅ: 274KZ Web of Science ºËÐĺϼ¯ÖÐµÄ "ÒýÓõIJο¼ÎÄÏ×": 37 Web of Science ºËÐĺϼ¯ÖÐµÄ "±»ÒýƵ´Î": 0 »¯Ñ§·´Ó¦ 1 ÖÁ 3 |
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rganocatalysis; chiral indanone; oxa-spirocycles; tandem reactions; asymmetric synthesis
IPHENYLPROLINOL SILYL ETHER; RECEPTOR ANTAGONISTS; 4 STEREOCENTERS; EFFICIENT; ADDITIONS; NITROALKENES; DERIVATIVES; ACTIVATION; CATALYSIS; ALDEHYDES