N1–C4 β-Lactam Bond Cleavage in the 2-(Trimethylsilyl)thiazole Addition to β-Lactam Aldehydes: Asymmetric Synthesis of Spiranic and Tertiary α-Alkoxy-γ-keto Acid Derivatives

2007 ◽  
Vol 2007 (22) ◽  
pp. 3707-3710 ◽  
Author(s):  
Benito Alcaide ◽  
Pedro Almendros ◽  
María C. Redondo
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Cleavage ◽  
Keto Acid

Asymmetric synthesis of 3-aryl-substituted 2,3-dihydro-1H-isoindol-1-ones

2001 ◽  
Vol 79 (11) ◽  
pp. 1528-1535 ◽  
Author(s):  
Dieter Enders ◽  
Volker Braig ◽  
Gerhard Raabe
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Cleavage ◽  
Oxidative Cleavage ◽  
Ring Closure

The first asymmetric synthesis of 3-aryl substituted 2,3-dihydro-1H-isoindol-1-ones via a tandem nucleophilic 1,2-addition ring closure procedure from SAMP and (or) RAMP hydrazones and subsequent oxidative cleavage of the auxiliary is reported.Key words: isoindolinones, asymmetric synthesis, hydrazones, 1,2-addition, N—N bond cleavage.

An evaluation of the substrate specificity and asymmetric synthesis potential of the cloned L-lactate dehydrogenase from Bacillusstearothermophilus

1989 ◽  
Vol 67 (6) ◽  
pp. 1065-1070 ◽  
Author(s):  
Daniel Bur ◽  
Marcel A. Luyten ◽  
Hla Wynn ◽  
Louis R. Provencher ◽  
J. Bryan Jones ◽  
...  
Keyword(s):  
Lactate Dehydrogenase ◽  
Asymmetric Synthesis ◽  
Expression Vector ◽  
Alkyl Chain ◽  
Keto Acid ◽  
Hydroxy Acids ◽  
Thermophilic Enzyme ◽  
Preparative Scale ◽  
Keto Acids ◽  
Branched Chain

The potential utility of the L-lactate dehydrogenase of Bacillusstearothermophilus (BSLDH) for stereospecific, preparative-scale reductions of α-keto acids to (S)-α-hydroxy acids of > 99% ee has been demonstrated. BSLDH is a stable, thermophilic, enzyme whose gene has been cloned into a high-expression vector to assure its plentiful supply. Its specificity for keto acid substrates possessing straight- and branched-chain alkyl, cyclopropyl, or phenyl groups has been evaluated in preparative and kinetic terms, and compared with that of the mammalian pig heart enzyme (PHLDH). The specificities of BSLDH and PHLDH are similar, with branched alkyl-chain keto acids being poor substrates for both enzymes. Keywords: enzymes in organic syntheses, lactate dehydrogenase, asymmetric synthesis.

Asymmetric synthesis of quaternary α-fluoro-β-keto-amines via detrifluoroacetylative Mannich reactions

2015 ◽  
Vol 51 (44) ◽  
pp. 9149-9152 ◽  
Author(s):  
Chen Xie ◽  
Yanling Dai ◽  
Haibo Mei ◽  
Jianlin Han ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Cleavage ◽  
Mannich Reactions

Asymmetric detrifluoroacetylative Mannich reactions of N-sulfinyl-imines via C–C bond cleavage were explored, which provide access to C–F quaternary α-fluoro-β-keto-amines.

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