Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles
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چکیده
منابع مشابه
Diastereoselective synthesis of potent antimalarial cis-β-lactam agents
Fifteen novel β-lactams bearing the N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by the ketene-imine [2+2] cycloaddition reaction (Staudinger ). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to the formation of the cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for the...
متن کاملDiastereoselective synthesis of potent antimalarial cis-β-lactam agents
Fifteen novel β-lactams bearing the N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by the ketene-imine [2+2] cycloaddition reaction (Staudinger ). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to the formation of the cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for the...
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Propargylamines are important intermediates for the synthesis of polyfunctional amino derivatives and natural products and biologically active compounds. The classic method of synthesizing chiral propargylamines involves the asymmetric alkynylation of imines. Here, we report a significant advance in the catalytic asymmetric Mannich-type synthesis of propargylamines through catalytic asymmetric ...
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The first synthesis of hydroxy-iso-evoninic acid (2), a pyridyl diacid found as a macrodilactone bridging ligand in bioactive Celastraceae sesquiterpenoid-based natural products, has been achieved in 9 steps and an overall yield of 26%. The synthesis utilizes a benzilic ester rearrangement (BER) and a late stage benzylic oxidation to give access to all four stereoisomers whose absolute stereoch...
متن کاملConcise and diastereoselective approach to syn- and anti-N-tosyl-a-hydroxy b-amino acid derivatives
The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy b-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give b-(N-tosyl)amino a-diazoesters, followed by oxidation with Oxone to generate a-oxo esters, which were reduced with NaBH4 to yield the ...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2017
ISSN: 1523-7060,1523-7052
DOI: 10.1021/acs.orglett.7b00679