Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
被引量：1
Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
摘要
The asymmetric allylic alkylation reaction of sulfonylimidates with various Morita-Baylis-Hillman(MBH)carbonates was accomplished by the catalysis of commercially available cinchona alkaloids catalyst(DHQD)2AQN.The corresponding allylic alkylation products were obtained in good yields with high stereoselectivities(up to 99%ee,89:11 dr).
基金
financially Supported by the National Natural Science Foundation of China(20772084)
参考文献28
-
1Feng X,Yuan YQ,Cui HL,Jiang K,Chen YC.Organocatalytic per- oxy-asymmetric allylic alkylation. Organic and Biomolecular Chemistry . 2009
-
2Zhang SJ,Cui HL,Jiang K,Li R,Ding ZY,Chen YC.Enantioselec- tive allylic amination of Morita-Baylis-Hillman carbonates catalysed by modified cinchona alkaloids. European Journal of Organic Chemistry . 2009
-
3Hu ZK,Cui HL,Jiang K,Chen YC.Enantioselective O-allylic alky- lation of Morita-Baylis-Hillman carbonates with oxime. Sci China Chem . 2010
-
4Larsen JD,Bundgaard H.Prodrug forms for the sulfonamide group III chemical and enzymatic hydrolysis of various N-sulfonyl imidates-a novel prodrug form for a sulfonamide group or an ester function. International Journal of Pharmaceutics . 1989
-
5Kupfer R,Nagel M,Würthwein EU,Allrnann R.Synthese und struktur von N-acylimidsaureestern. Chemische Berichte . 1985
-
6Matsubara R,Berthiol F,Kobayashi S.Sulfonylimidates as nucleo- philes in catalytic addition reactions. Journal of the American Chemical Society . 2008
-
7Matsubara R,Kobayashi S.DBU-catalyzed addition reactions of sul- fonylimidates. Synthesis . 2008
-
8Kan SBJ,Matsubara R,Berthio F,Kobayashi S.Catalytic direct-type substitution reaction of α-alkyl enolates: A Pd/Br nsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates. Chemical Communications . 2008
-
9Nguyen HV,Matsubara R,Kobayashi S.Addition reactions of sul- fonylimidates with imines catalyzed by alkaline earth metals. Angewandte Chemie International Edition . 2009
-
10Massa A,Utsumi N,Barbas III CF.N-tosylimidates in highly enanti- oselective organocatalytic michael reactions. Tetrahedron Letters . 2009
同被引文献10
-
1Faye Maertens, Suzanne teppet, Frans compemolle. Incorporation of diarylbutylamine pharmacophore into indeno- or naphtho [ 1,2-b ] pyran Ring Systems [ J ]. Eur J Org Chem,2004:2707-2714.
-
2Eugene G, Tamar Y, Alfred H. Utilization of ethyl 2-[(phenylsulfonyl) methyl ] acrylate for the synthesis of a-methylenevaIerolactones [ J ]. J Org Chem, 1990, 55 (24) :5977 -5982.
-
3Carlos A M Fraga, Lis Helena P Teixeira, Carla Mafia de S Menezes, et al. Studies on diastereoselective re- duction of cyclic β-ketoesters with boron hydrides. Part 4:The reductive profile of functionalized cyclohexanone derivatives [ J ]. Tetrahedron,2004,60: 2745 - 2755.
-
4Cui H L, Peng J, Chen Y C. etal. Dual organocatalysis : Asymmetric anylic-allylic alkylation of a, a-dicyanoalkenes and Morita-Baylis-Hilhnan carbonates [J].Chem Eur J,2009,15 : 1574 - 1577.
-
5Peng J, Huang X, Chen Y C. Organocatalytic and electrophilic approach to oxindoles with C3-quaternary stereocenters [ J ]. Org Lett, 2010, 12 ( 19 ) : 4260 - 4263.
-
6House H O, Hudson C B. Perhysro indan derivatives Ⅻ6-Methoxyindanone and its derivatives [ J]. J Org Chem, 1970,35 ( 8 ) : 647 - 651.
-
7Jack K Crandall, Chrostian Pradat. Synthesis of Sulfones by phase-transfer alkylation of arenesulfinate salts[J]. J Org Chem,1985,50(8) :1327 - 1329.
-
8Feng J, Lu X, Kong A, etal. A highly regio- and stero-selective [ 3 + 2 ] annulation of allylic com- pounds and 2-substituted 1,1-dicyanoalkenes through a catalytic carbo-phosphorus ylid reaction[ J ]. Tetra- hedron,2007,63:6035 - 6041.
-
9D Y S, Hart X L, Lu X Y. Alkaloids-catalyzed regio- and enant/o-se]ectlve allylic nucleophilic substitution of tert-butyl carbonate of the Morit-Bayllc-Hillman products [ J ]. Tetrahedron Left, 2004, 45: 4967 - 4971.
-
10方玲,石岩,朱成建.有机小分子催化的β-酮酯不对称α-官能化反应[J].化学进展,2010,22(9):1679-1686. 被引量：1
-
1HU ZeKai,CUI HaiLei,JIANG Kun,CHEN YingChun.Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime[J].Science China Chemistry,2009,52(9):1309-1313. 被引量：1
-
2胡泽锴,崔海磊,蒋堃,陈应春.Morita-Baylis-Hillman碳酸酯与肟的对映选择性O-烯丙基烷基化反应[J].中国科学（B辑）,2009,39(9):979-979.
-
3武陈,曾皓,刘哲,刘利,王东,陈拥军.FeCl_(3-) and GaCl_(3-) Catalyzed Dehydrative Coupling Reaction of Chromone-Derived Morita-Baylis-Hillman Alcohols with Terminal Alkynes[J].Chinese Journal of Chemistry,2011,29(12):2732-2738.
-
4QI ChaoRong,JIANG HuanFeng.Histidine-catalyzed synthesis of cyclic carbonates in supercritical carbon dioxide[J].Science China Chemistry,2010,53(7):1566-1570. 被引量：3
-
5Li Ferg GENG,Xi Yan LU.PALLADIUM CATALYZED REACTION OF 3-TRIMETHYLSILYLPROPARGYLIC CARBONATES WITH DINUCLEOPHILES[J].Chinese Chemical Letters,1991,2(8):595-596.
-
6吴昊,巫循伟,侯雪龙,戴立信,王全瑞.New Chiral N,S-Ligands with Thiophenyl at Benzylic Position. Palladium(II)-catalyzed Enantioselective Allylic Alkylation[J].Chinese Journal of Chemistry,2002,20(9):816-818.
-
7GENG,Li-Feng LU,Xi-Yan Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032.Palladium(0)catalyzed reactions of propargylic carbonates and dialkyl cycloalkanone-α,α-dicarboxylates[J].Chinese Journal of Chemistry,1993,11(1):91-94.
-
8张龙,罗三中,陈柳娟,李九远,程津培.手性伯胺-叔胺二胺化合物双功能催化BaylisHillman反应：非经典的催化历程[J].中国科学（B辑）,2009(9):978-978.
-
9Hong-Yu Duan,Juan Ma,Zhe-Zhe Yuan,Ri-Sheng Yao,Wei Tao,Fang Xu,Hua Xiao,Gang Zhao.Phosphine-promoted [3+2] cycloaddition between nonsubstituted MBH carbonates and trifluoromethyl ketones[J].Chinese Chemical Letters,2015,26(6):646-648. 被引量：2
-
10MA Xiaoyuan,WU Yi,ZHANG Yanjing,TENG Lesheng,XIE Jing,LIAO Weiwei.Regioselective Synthesis of Functionalized Dihydroquinolines via Organocatalytic Allylic Alkylation[J].Chemical Research in Chinese Universities,2016,32(4):634-640.
