- Enantioselective Total Synthesis of Nitraria Alkaloids: (+)-Nitramine, (+)-Isonitramine, (-)-Isonitramine, and (-)-Sibirine via Asymmetric Phase-Transfer Catalytic α-Allylations of α-Carboxylactams
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Many optically active 2-azaspirocyclic structures have frequently been found in biologically active natural products. In particular, Nitraria alkaloids, (+)-nitramine, (+)-isonitramine, (-)-isonitramine, and (-)-sibirine, have stereogenicity on their quat
- Yang, Jewon,Park, Yohan,Yang, Sehun,Lee, Geumwoo,Ha, Min Woo,Kim, Mi-Hyun,Hong, Suckchang,Park, Hyeung-Geun
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p. 4375 - 4390
(2021/02/05)
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- Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains
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N-Benzyloxycarbonyl (Cbz)-protected 2-aminoalkanesulfonyl chlorides are useful building blocks for the synthesis of sulfonopeptides, which are receptor ligands and enzyme inhibitors, and are prepared by the coupling reaction of N-protected aminoalkanesulfonyl chlorides with amino acid or peptide esters. Various N-Cbz-protected 2-aminoalkanesulfonyl chlorides with functionalized side chains were synthesized through the radical addition of different xanthates to benzyl N-allylcarbamate and subsequent oxidative chlorination with tert-butyl hypochlorite under neutral conditions. A mechanism for the oxidative chlorination is proposed. This is a useful and convenient strategy for the synthesis of N-Cbz-protected 2-aminoalkanesulfonyl chlorides with diverse functionalized side-chains.
- Abdellaoui, Hassane,Chen, Xingpeng,Xu, Jiaxi
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p. 2250 - 2256
(2017/05/05)
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- Cascade synthesis of spirooxindole δ-lactone derivatives through N-aryl hydroxymethylacrylamides with xanthates
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A novel and highly efficient cascade synthesis of spirooxindole δ-lactone derivatives from N-aryl hydroxymethylacrylamides and xanthates in good yields is described. The reaction proceeds through a radical addition/cyclization and ester exchange, in which two new C-C bonds and one C-O bond were formed.
- Wang, Shucheng,Huang, Xuhu,Wen, Yanzhao,Ge, Zemei,Wang, Xin,Li, Runtao
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supporting information
p. 8117 - 8122
(2015/12/30)
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- One-pot synthesis of symmetric 1,7-dicarbonyl compounds via a tandem radical addition-elimination-addition reaction
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A novel approach to synthesize symmetric 1,7-dicarbonyl compounds via a tandem radical addition-elimination-addition reaction of S-carbonylmethyl xanthates with allylmethylsulfone and its analogues has been developed. Radicals were produced from S-carbonylmethyl xanthates by adding dilauroyl peroxide and reacted with allylmethylsulfone or analogues to generate terminal olefins as intermediates. The excessive radicals reacted with the intermediate olefins immediately to give adducts of symmetric 1,7-dicarbonyl compounds. This is an efficient method to synthesize 1,7-dicarbonyl compounds under mild conditions. The Royal Society of Chemistry 2013.
- Huang, Zhongyan,Xu, Jiaxi
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p. 15114 - 15120
(2013/09/02)
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- Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains
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A radical addition reaction and subsequent performic acid oxidation were used for the synthesis of 1-substituted taurines with diverse functionalized side-chains from N-allylphthalimide and various xanthates. The current approach shows high yields and short synthetic route and reaction time. Moreover, the current method is a convenient and practical method for the synthesis of 1-substituted taurines with different functionalized side-chains.
- Kakaei, Saeed,Chen, Ning,Xu, Jiaxi
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supporting information
p. 302 - 309
(2013/01/15)
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- Highly enantioselective total synthesis of (+)-isonitramine
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A new efficient enantioselective synthetic method of (+)-isonitramine is reported. (+)-Isonitramine was obtained in 12 steps (98% ee and 43% overall yield) from δ-valerolactam via enantioselective phase-transfer catalytic alkylation, Dieckman condensation
- Park, Yohan,Lee, Young Ju,Hong, Suckchang,Lee, Myungmo,Park, Hyeung-Geun
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supporting information; experimental part
p. 852 - 854
(2012/04/05)
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- Free-radical carboalkynylation and carboalkenylation of olefins
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Free-radical three-component carboalkynylation and -alkenylation of olefins have been developed. These involve the addition, across the double bond of an unactivated olefin, of a radical species α- to an electron-withdrawing group and an alkenyl or alkynyl moiety, derived from the corresponding sulfones.
- Liautard, Virginie,Robert, Frederic,Landais, Yannick
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supporting information; experimental part
p. 2658 - 2661
(2011/06/26)
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- Synthesis of azepino[4,5-b]indolones via an intermolecular radical oxidative substitution of N-Boc tryptamine
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A two-step protocol for the synthesis of azepino[4,5-b]indolone derivatives featuring a xanthate radical oxidative aromatic substitution on the N-Boc protected tryptamine, using dilauroyl peroxide (DLP) as initiator and oxidant, is described.
- Reyes-Gutierrez, Paul E.,Torres-Ochoa, Ruben O.,Martinez, Robertoz,Miranda, Luis D.
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experimental part
p. 1388 - 1396
(2009/12/04)
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- Intramolecular schmidt reaction involving primary azidoalcohols under nonacidic conditions: Synthesis of indolizidine (-)-167B
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(Chemical Equation Presented) A powerful intramolecular Schmidt reaction starting from primary azidoalcohols is reported. This approach involves a nonacidic activation of the alcohol via triflation. The synthetic potential offered by the mild reaction con
- Kapat, Ajoy,Nyfeler, Erich,Giuffredi, Guy T.,Renaud, Philippe
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supporting information; experimental part
p. 17746 - 17747
(2010/04/01)
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- Synthesis and Insecticidal Activity of Oxazaphospholidines, Oxathiaphospholanes, and Thiazaphospholidines
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Fifty-five new five-membered cyclic organophosphorus compounds including oazaphospholidines, thiazaphospholidines, and oxathiaphospholanes were synthesized, which have substituents at 4- or/and 5-positions besides at the 2-position.The thiazaphospholidines showed the highest insecticidal activity followed by oxathiaphospholanes and oxazaphospholidines.The position preference of substituents in insecticidal activity was most obvious in the oxazaphospholidines.It was preferable for insecticidal activity to have the substituent near the more basic atom: the 4-position for thiazaphospholidine and oxazaphospholidine, the 5-position for oxathiaphospholane, with the exception of 4- or 5-phenyl oxazaphospholidine.
- Wu, Shao-Yong,Hirashima, Akinori,Takeya, Ryuko,Eto, Morifusa
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p. 2911 - 2918
(2007/10/02)
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