Catalytic asymmetric coupling of vinylogous species via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles.

An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. With quinine-derived bifunctional squaramide as the catalyst, a series of structurally diverse enantioenriched sec-alkyl-3-substituted indoles containing valuable γ,γ-disubstituted butenolide moieties and adjacent quaternary-tertiary stereocenters are obtained in synthetically viable results (up to 97% yield, 77 : 23 dr and 97% ee).

[1]  S. S. Chimni,et al.  Arenesulfonyl indole: new precursor for diversification of C-3 functionalized indoles , 2021, RSC advances.

[2]  Jian‐Qiang Zhao,et al.  Organocatalytic asymmetric tandem α-functionalization/1,3-proton shift reaction of benzylidene succinimides with β-trifluoromethyl enones. , 2020, Chemical communications.

[3]  S. Mukherjee,et al.  Deconjugated butenolide: a versatile building block for asymmetric catalysis. , 2020, Chemical Society reviews.

[4]  N. Kumagai,et al.  Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones , 2020, Chemical science.

[5]  B. Trost,et al.  Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol. , 2019, Journal of the American Chemical Society.

[6]  Bin Mao,et al.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones , 2017, Chemical reviews.

[7]  Yi‐Xia Jia,et al.  Recent progress in transition-metal-catalyzed enantioselective indole functionalizations. , 2017, Organic & biomolecular chemistry.

[8]  Jeng‐Liang Han,et al.  Organocatalytic Enantioselective Friedel‐Crafts Reaction of Sesamol and Electron–rich Phenols with Alkylideneindolenine Intermediates Generated from Arylsulfonyl Indoles , 2016 .

[9]  L. Gong,et al.  Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B. , 2015, Chemistry.

[10]  Renato Dalpozzo,et al.  Strategies for the asymmetric functionalization of indoles: an update. , 2015, Chemical Society reviews.

[11]  Yong‐Gui Zhou,et al.  Rhodium-Catalyzed Addition of Boronic Acids to Vinylogous Imines Generated in situ from Sulfonylindoles , 2011 .

[12]  Lili Lin,et al.  Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone. , 2011, Organic letters.

[13]  G. Fabrizi,et al.  Update 1 of: Synthesis and functionalization of indoles through palladium-catalyzed reactions. , 2011, Chemical reviews.

[14]  Yucheng Gu,et al.  Triterpenoids from Aglaia abbreviata and their cytotoxic activities. , 2010, Journal of natural products.

[15]  G. Bartoli,et al.  Organocatalytic strategies for the asymmetric functionalization of indoles. , 2010, Chemical Society reviews.

[16]  Lin-Hai Jing,et al.  Highly enantioselective Michael addition of malononitrile to vinylogous imine intermediates generated in situ from arylsulfonyl indoles. , 2010, Chemistry.

[17]  M. Hamann,et al.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety. , 2010, Chemical reviews.

[18]  J. Campagne,et al.  Organocatalyzed Asymmetric Friedel–Crafts Reactions , 2010 .

[19]  Chang-Hua Ding,et al.  Ag-Catalyzed diastereo- and enantioselective synthesis of beta-substituted tryptophans from sulfonylindoles. , 2010, Organic letters.

[20]  Li Wu,et al.  Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates. , 2010, Organic letters.

[21]  M. Zeng,et al.  Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reactions. , 2009, Chemical Society reviews.

[22]  A. Mazzanti,et al.  Proline-catalyzed asymmetric formal alpha-alkylation of aldehydes via vinylogous iminium ion intermediates generated from arylsulfonyl indoles. , 2008, Angewandte Chemie.

[23]  R. Süssmuth,et al.  Action of atrop-abyssomicin C as an inhibitor of 4-amino-4-deoxychorismate synthase PabB. , 2007, Angewandte Chemie.

[24]  Scott T. Harrison,et al.  Total synthesis of abyssomicin C, atrop-abyssomicin C, and abyssomicin D: implications for natural origins of atrop-abyssomicin C. , 2007, Journal of the American Chemical Society.

[25]  A. Palmieri,et al.  Solventless clay-promoted Friedel-Crafts reaction of indoles with alpha-amido sulfones: unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles. , 2006, Organic letters.

[26]  Lin-Hai Jing,et al.  Organocatalytic Asymmetric Michael Addition of Oxazolones to Arylsulfonyl Indoles: Facile Access to syn‐Configured α,β‐Disubstituted Tryptophan Derivatives , 2013 .

[27]  M. Ishikura,et al.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. , 2010, Natural product reports.

[28]  M. Ishikura,et al.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. , 2009, Natural product reports.

[29]  T. Kawasaki,et al.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. , 2005, Natural product reports.