α-Amino 1,3-dithioketal mediated asymmetric synthesis of piperidines (L-733,060) and tetrahydrofuran glycines
نویسندگان
چکیده
منابع مشابه
α-Vinylic amino acids: occurrence, asymmetric synthesis, and biochemical mechanisms
This report presents an overview of the family of naturally occurring “vinylic” amino acids, namely those that feature a C–C double bond directly attached to the α-carbon, along the side chain. Strategies that have been brought to bear on the stereocontrolled synthesis of these olefi nic amino acids are surveyed. The mechanistic diversity by which such “vinylic triggers” can be actuated in a PL...
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Previously, we reported an efficient asymmetric synthesis of substituted piperidines through an exocyclic chirality induced nitroalkene/amine/enone (NAE) condensation reaction. An effective protecting group strategy was developed herein to achieve enantiopure piperidines (yields up to 92%) with complete chirality retention (ee > 95%). A simple derivatization of the obtained piperidines gave thi...
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The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alter...
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The bis-THF cores of annonaceous acetogenins were synthesized using (3R,4R)-1,5-hexadiene-3,4-diol (1) as the sole source of carbon atoms. The methylene acetal function was applied as a new linker/tether to facilitate the ring-closing metathesis.
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A variety of chiral N-phosphinyl α-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected α-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtai...
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ژورنال
عنوان ژورنال: Tetrahedron Letters
سال: 2008
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2007.11.170