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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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dala1990: ½ð±Ò+5, ¡ï¡ï¡ïºÜÓаïÖú, ÄúºÃ£¬ÇëÎÊÄܲ»ÄÜÔÙ°ïÎÒ¿´¿´¼ìË÷ºÅÄØ¡£Ð»Ð»ÁË¡£ 2014-03-03 10:27:00
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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 ]




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¾í: 25

ÆÚ: 1

Ò³: 143-147

DOI: 10.1055/s-0033-1340077

³ö°æÄê: JAN 2 2014

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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´Êrganocatalysis; chiral indanone; oxa-spirocycles; tandem reactions; asymmetric synthesis

KeyWords PlusIPHENYLPROLINOL 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

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GEORG THIEME VERLAG KG, RUDIGERSTR 14, D-70469 STUTTGART, GERMANY


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Ñо¿·½Ïò:Chemistry

Web of Science Àà±ð:Chemistry, Organic


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ÎÄÏ×ÀàÐÍ:Article

ÓïÖÖ:English

Èë²ØºÅ: WOS:000328606500024

ISSN: 0936-5214

µç×Ó ISSN: 1437-2096


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Impact Factor (Ó°ÏìÒò×Ó): Journal Citation Reports®


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IDS ºÅ: 274KZ

Web of Science ºËÐĺϼ¯ÖÐµÄ "ÒýÓõIJο¼ÎÄÏ×": 37

Web of Science ºËÐĺϼ¯ÖÐµÄ "±»ÒýƵ´Î": 0









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