Welcome To WUJNS
武汉大学学报 英文版 | Wuhan University Journal of Natural Sciences
Wan Fang
Wuhan University
Latest Article
Enantioselective Chlorocyclization of Olefinic Amides with 1,3-Dichloro- 5, 5-Dimethylhydantoin (DCDMH) Catalyzed by (DHQD)2PHAL
ZHOU Qingjun, GUO Chao, LI Xiwang, HE Pei, YANG Guichun, DONG Chune
1. Hubei Collaborative Innovation Center for Advanced Organochemical Materials & Ministry of Education Key Labora-tory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, Hubei, China; 2. School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, Hubei, China
An efficient catalytic asymmetric chlorocyclization of olefinic amides with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using hydroquinidine 1,4-phthalazinediyl diether ((DHQD)2PHAL) as organocatalyst has been developed. Series of chiral chloro substituted isobenzofuran-1(3H)-imine derivatives were obtained in good yields (up to 85%) and enantioselectivities (up to 70% ee).
Key words:Asymmetric chlorocyclization; olefinic amides; 1,3-dichloro-5, 5-dimethylhydantoin(DCDMH)
CLC number: TP 305
[1]	French A N, Bissmire S, Wirth T. Iodine electrophiles in stereoselective reactions: Recent developments and synthetic applications [J]. Chem Soc Rev, 2004, 35(44): 354-362.
[2]	Denmark S E, Kuester W E, Burk M T. Catalytic, asymmet-ric halofunctionalization of alkenes—A critical perspective [J]. Angew Chem Int Ed, 2012, 51(44): 10938-10953.
[3]	Dobish M C, Johnston J N. Achiral counterion control of enantioselectivity in a Bronsted acid-catalyzed iodolactoni-zation [J]. J Am Chem Soc, 2012, 134(14): 6068-6071. 
[4]	Zhou L, Tan C K, Jiang X, et al. Asymmetric bromolactonization using amino-thiocarbamate catalyst [J]. J Am Chem Soc, 2010, 132(44): 15474-15476. 
[5]	Fang C, Paull D H, Hethcox J C, et al. Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst [J]. Org Lett, 2012, 14(24): 6290-6293. 
[6]	Murai K, Matsushita T, Nakamura A, et al. Kinetic resolution of β-substituted olefinic carboxylic acids by asymmetric bromolactonization [J]. Organic Letters, 2013, 15(10): 2526- 2529. 
[7]	Chen J, Zhou L, Tan C K, et al. An enantioselective ap-proach toward 3,4-dihydroisocoumarin through the bromo-cyclization of styrene-type carboxylic acids  [J]. J Org Chem, 2012, 43(21): 999-1009. 
[8]	Tan C K, Le C, Yeung Y Y. Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino- thiocarbamate catalyst [J]. Chem Commun, 2012, 48(46): 5793- 5795. 
[9]	Murai K, Nakamura A, Matsushita T, et al. C3-symmetric trisimidazoline-catalyzed enantioselective bromolactoniza-tion of internal alkenoic acids [J]. Chem Eur J, 2012, 18(27): 8448- 8453. 
[10]	Ikeuchi K, Ido S, Yoshimura S, et al. Catalytic desymmetrization of cyclohexadienes by asymmetric bromolactonization [J]. Org Lett, 2012, 14(23): 6016-6019. 
[11]	Wilking M, Muck-Lichtenfeld C, Daniliuc C G, et al. Enan-tioselective, desymmetrizing bromolactonization of alkynes [J]. J Am Chem Soc, 2013, 135(22): 8133-8136. 
[12]	Veitch G E, Jacobsen E N. Tertiary aminourea-catalyzed enantioselective iodolactonization [J]. Angew Chem Int Ed, 2010, 49(40): 7332-7335. 
[13]	Tungen J E, Nolsoe J M, Hansen T V. Asymmetric iodolac-tonization utilizing chiral squaramides [J]. Org Lett, 2012, 14 (23): 5884-5887. 
[14]	Paull D H, Fang C, Donald J R, et al. Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds [J]. J Am Chem Soc, 2012, 134(27): 11128-11131.
[15]	Huang H, Zhu X, He G, et al. Controlled synthesis of 1, 3, 5-oxadiazin-2-ones and oxazolones through regioselective iodocyclization of ynamides [J]. Org Lett, 2015, 17(10): 2510-2513.
[16]	Cheng Y A, Yu W Z, Yeung Y Y. An unexpected bromolac-tamization of olefinic amides using a three-component co-catalyst system [J]. J Org Chem, 2015, 81(2): 545-552.
[17]	Zhang W, Liu N, Schienebeck C M, et al. Catalytic enanti-oselective halolactonization of enynes and alkenes [J]. Chem Eur J, 2012, 18(23): 7296-7305.
[18]	Deng J, Yu S N, Li Y L. Enantioselective synthesis of 2-bromomethyl indolines via BINAP (S)-catalyzed bromo-aminocyclization of allyl aniline [J]. Adv Synth & Catal, 2017, 359(14): 2499-2508.
[19]	Commercon A, Ponsinet G. Diastereoselective chlorocyclo-functionalization of N-allylic trichloroacetamides: Synthesis of an analogue and potential precursor of RP49532 [J]. Tetrahedron Lett, 1990, 31 (27): 3871-3874.
[20]	Whitehead D C, Yousefi R, Jaganathan A, et al. An organocatalytic asymmetric chlorolactonization [J]. J Am Chem Soc, 2010, 132(10): 3298-3300.
[21]	Yousefi R, Whitehead D C, Mueller J M, et al. On the chlorenium source in the asymmetric chlorolactonization reaction [J]. Org Lett, 2011, 13(4): 608-611.
[22]	Fei N, Yin H, Wang S, et al. CuCl2-promoted 6-endo-dig chlorocyclization and oxidative aromatization cascade: efficient construction of 1-azaanthraquinones from N-propargylaminoquinones[J]. Org Lett, 2011, 13(16): 4208- 4211.
[23]	Jaganathan A, Staples R J, Borhan B. Kinetic resolution of unsaturated amides in a chlorocyclization reaction: concomitant enantiomer differentiation and face selective alkene chlorination by a single catalyst [J]. J Am Chem Soc, 2013, 135(39): 14806-14813.
[24]	Jaganathan A, Borhan B. Chlorosulfonamide salts are superior electrophilic chlorine precursors for the organocatalytic asymmetric chlorocyclization of unsaturated amides [J]. Org Lett, 2014, 16(14): 3616-3619.
[25]	Yu Y M, Huang Y N, Deng J. Catalytic asymmetric chloro-cyclization of 2-vinylphenylcarbamates for synthesis of 1, 4-dihydro-2H-3, 1-benzoxazin-2-one derivatives [J]. Org Lett, 2017, 19 (5): 1224-1227.
[26]	Han X, Zhou H B, Dong C E. Application of chiral squara-mides from asymmetric organocatalysts to biologically active compounds [J]. Chem Rec, 2016, 16(2): 897-906.
[27]	Lü W, Guo C, Dong Z, et al. C3-symmetric cincho-nine-squaramide recyclable efficient organocatalyst for tandem Michael addition-cyclization of malononitrile and nitrovinylphenols [J]. Tetrahedron: Asymmetry, 2016, 27(14- 15): 670-674.
[28]	Gao Y, Liu B, Zhou H B, et al. Recyclable BINOL-quinine- squaramide as highly efficient organocatalyst for α-amination of 1,3-dicarbonyl compounds and α-cyanoacetates [J]. RSC Adv, 2015, 5: 24392-24398.
[29]	Han X, Dong C E, Zhou H B. C3-Symmetric cinchonine- squaramide-catalyzed asymmetric chlorolactonization of styrene-type carboxylic acids with 1,3-dichloro-5, 5-dimethylhydantoin: An efficient method to chiral isochroman-1-ones [J]. Adv Synth Catal, 2014, 356 (6): 1275-1280.
[30]	Jaganathan A, Garzan A, Whitehead D C, et al. A catalytic asymmetric chlorocyclization of unsaturated amides [J]. Angew Chem Int Ed, 2011, 50 (11): 2593-2596.
[31]	Toshimitsu A, Terao K, Uemura S. Organoselenium-induced cyclization of olefinic imidates and amides: Selective synthesis of lactams or iminolactones [J]. J Org Chem, 1987, 52(10): 2018-2026.
Welcome To WUJNS

HOME | Aim and Scope | Editoral Board | Current Issue | Back Issue | Subscribe | Crosscheck | Polishing | Contact us Copyright © 1997-2019 All right reserved