Pyruvate Aldolases Catalyze Cross-Aldol Reactions between Ketones: Highly Selective Access to Multi-Functionalized Tertiary Alcohols
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چکیده
منابع مشابه
Highly Diastereoselective Aldol Reactions of Chiral Methyl Ketones
Diastereoselective aldol additions have emerged as one of the most efficient and versatile methods available for preparing a wide range of optically active compounds.l Very high diastereoselectivities have been reported for aldol reactiona involving chiral enolates derived from a-ethylor higher alkyl-substituted ketone derivatives. By contrast, relatively few examples of highly diastereoselecti...
متن کاملMimicking aldolases through organocatalysis: syn-selective aldol reactions with protected dihydroxyacetone.
A practical organocatalytic strategy designed to mimic the l-rhamnulose 1-phosphate and D-fructose 1,6-diphosphate aldolases has been developed and shown to be effective in the preparation of carbohydrates and polyol derivatives. Threonine-based catalysts facilitated the aldol reaction of protected dihydroxyacetone or protected hydroxacetone with a variety of aldehydes to provide syn-aldol prod...
متن کاملIron-catalyzed cross-aldol reactions of ortho-diketones and methyl ketones.
Iron-catalyzed cross-aldol reactions of ortho-diketones and methyl ketones were developed and the thus formed aldol products were efficiently transformed into cyclohepta-2,4,6-trienone derivatives (tropones) under thermal conditions via ring-expansion.
متن کامل(S)-Selective MenD variants from Escherichia coli provide access to new functionalized chiral α-hydroxy ketones.
We report the first rationally designed (S)-selective MenD from E. coli for the synthesis of functionalized α-hydroxy ketones. By mutation of two amino acids in the active site stereoselectivity of the (R)-selective EcMenD (ee > 93%) was inverted giving access to (S)-5-hydroxy-4-oxo-5-phenylpentanoate derivatives with stereoselectivities up to 97% ee.
متن کاملEnantioselectivity in the boron aldol reactions of methyl ketones.
DFT computed transition states quantitatively explain the surprising stereochemical outcome of unsubstituted enolborinates in diastereoselective and enantioselective boron aldol reactions.
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ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2020
ISSN: 2155-5435,2155-5435
DOI: 10.1021/acscatal.9b05512