20261-68-1Relevant articles and documents
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Bunnett,Tarbell
, p. 1944 (1945)
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SYNTHESIS OF 1-CHLORO-2-ALKANONES USING MELDRUM'S ACID
Zav'yalov, S. I.,Ezhova, G. I.,Budkova, T. K.
, p. 1780 (1981)
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Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent "ene"-Reductases
Gao, Xin,Turek-Herman, Joshua R.,Choi, Young Joo,Cohen, Ryan D.,Hyster, Todd K.
supporting information, p. 19643 - 19647 (2021/12/01)
α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent ‘ene'-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.
Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine
Ema, Tadashi,Ura, Norichika,Yoshii, Masataka,Korenaga, Toshinobu,Sakai, Takashi
experimental part, p. 9583 - 9591 (2010/01/06)
We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).
A general synthesis of enantiopure 1,2-aminoalcohols via chiral morpholinones
Segat-Dioury, Fabienne,Lingibé, Olivier,Graffe, Bernadette,Sacquet, Marie-Claude,Lhommet, Gérard
, p. 233 - 248 (2007/10/03)
Eleven optically active 1,2-aminoalcohols 20a-i and 26b-c were prepared from D-phenylglycine via cyclic imines 7b-i (or enamine 7a). The key step of the strategy is the diastereoselective reduction of chiral oxazinones 7a-i.