- Aminolithiation–arylation consecutive cyclization of N-(2-fluorophenyl)methylaminoalkylstyryls giving aryl-substituted pyrido[1,2-b]isoquinolines
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Aminolithiation–arylation tandem cyclization of N-(2-fluorophenyl)methylaminoalkylstyryls proceeded smoothly to give hexahydro-2H-pyrido[1,2-b]isoquinoline using a stoichiometric amount of n-BuLi with high trans selectivity. The arylation reaction was highly accelerated by the addition of HMPA. Both pyrido- and pyrrolo-[1,2-b]isoquinoline were successfully constructed by this tandem reaction.
- Yamamoto, Yasutomo,Nakanishi, Yasue,Yamada, Ken-ichi,Tomioka, Kiyoshi
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supporting information
p. 5309 - 5318
(2018/06/11)
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- One-pot synthesis of α-amino acids from CO2 using a bismetal reagent with Si-B bond
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In the presence of 1.1 equiv of PhMe2Si-Bpin, 5 equiv of CsF, and 20 mol % of TsOH·H2O, precursors of N-Boc-imines can be converted into the corresponding α-aryl or α-alkenyl glycine derivatives under gaseous CO2 in moderate-to-high yields with a single operation. α-Isobutenyl glycine thus obtained can be further derivatized into various types of α-amino acids including N-Boc-leucine, serine, and glycine derivatives in short steps.
- Mita, Tsuyoshi,Chen, Jianyang,Sugawara, Masumi,Sato, Yoshihiro
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p. 6202 - 6205
(2013/02/23)
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- One-pot synthesis of α-amino acids from imines through CO2 incorporation: An alternative method for strecker synthesis
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Itas a gas: A novel one-pot process for the synthesis of α-amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl.
- Mita, Tsuyoshi,Chen, Jianyang,Sugawara, Masumi,Sato, Yoshihiro
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p. 1393 - 1396
(2011/04/22)
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- Synthesis and application of a new fluorous-tagged ammonia equivalent
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A novel fluorous-tagged ammonia equivalent has been developed. It is based on a nitrogen-oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluo-rous N-O linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.
- Nielsen, Simon D.,Smith, Garrick,Begtrup, Mikael,Kristensen, Jesper L.
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supporting information; experimental part
p. 4557 - 4566
(2010/08/20)
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- DPP-IV INHIBITORS
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The invention relates to compounds of formula (I), Z-C(R1R 2)-C(R3NH2)-C(R4R5)-X-N(R 6R7), wherein Z, R1-7 and X have the meaning as cited in the description and the claims. Said compounds are useful as DPP-lV inhibitors. The invention also relates to the
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Page/Page column 40
(2010/02/14)
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- Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions
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We report a novel and efficient method for the enantioselective synthesis of N-Boc protected phenylglycines. Yields and enantiomeric ratios vary widely depending on the nature of the solvent, the substrate and on the method of forming the chiral complex. Results show that the major reaction pathway is an enantioselective deprotonation/substitution process. The enantioselectivity appears to be limited by the chiral discrimination ability of the s-BuLi-(-)-sparteine complex. The synthetic method described is one of the shortest route to useful enantioenriched N-Boc phenylglycine derivatives.
- Barberis, Claude,Voyer, Normand,Roby, Johanne,Chénard, Sylvain,Tremblay, Martin,Labrie, Philippe
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p. 2965 - 2972
(2007/10/03)
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