97551-19-4Relevant articles and documents
Synthesis of Chiral Alkenyl Cyclopropane Amino Acids for Incorporation into Stapled Peptides
Yuen, Tsz Ying,Brown, Christopher J.,Tan, Yaw Sing,Johannes, Charles W.
, p. 1556 - 1566 (2020)
α,α′-Disubstituted amino acids serve as important non-proteinogenic amino acids in the construction of stabilized helical peptides. To expand the repertoire of α,α′-disubstituted amino acids, chiral alkenyl-containing cyclopropane amino acids were synthes
Rearrangement of N- tert-Butanesulfinyl Enamines for Synthesis of Enantioenriched α-Hydroxy Ketone Derivatives
Li, Chun-Tian,Liu, Hui,Yao, Yun,Lu, Chong-Dao
, p. 8383 - 8388 (2019/10/14)
Treating chiral N-tert-butanesulfinyl ketimines with potassium hexamethyldisilazide (or potassium tert-butoxide) and methyl triflate gives N-methylated N-tert-butanesulfinyl enamine intermediates that undergo stereoselective [2,3]-rearrangement to afford α-sulfenyloxy ketones with excellent enantiopurities. This cascade of enamination-N-methylation-rearrangement was even used to generate acyclic tertiary α-hydroxy ketones bearing two α-substituents showing negligible differences in bulkiness, such as methyl and ethyl groups.
BUILDING BLOCKS FOR STAPLED PEPTIDES
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Paragraph 00097; 00099, (2018/10/19)
This invention relates to a method for producing an alkenyl 1 -aminocyclopropane-1 -carboxylic acid of Formula I wherein R1 is a protecting group, n is an integer between 1 and 10, and A and B are chiral centres such that when A is S, B is R an
Benzaldehyde lyase-catalyzed diastereoselective C-C bond formation by simultaneous carboligation and kinetic resolution
Müller, Christoph R.,Pérez-Sánchez, María,Domínguez De María, Pablo
supporting information, p. 2000 - 2004 (2013/05/22)
Enzymes create chiral microenvironments that may simultaneously generate several stereogenic centers in the same catalytic cycle, broadening the possibilities of biocatalysis. Benzaldehyde lyase (BAL) affords highly diastereoselective α-hydroxy-ketones by simultaneously performing ligation and kinetic resolution of a racemic aldehyde. Thus, to the well-known enantioselective BAL-carboligation of aldehydes (C-C bond formation), another property, namely diastereoselectivity, is added in this paper for the first time.
Metallophosphites as Umpolung Catalysts: The Enantioselective Cross Silyl Benzoin Reaction
Linghu, Xin,Potnick, Justin R.,Johnson, Jeffrey S.
, p. 3070 - 3071 (2007/10/03)
Carbonyl polarity reversal (umpolung) has been realized employing metallophosphites as catalysts. As a result, nonenzymatic asymmetric cross silyl benzoin reactions have been achieved, giving optically active silyl ether-protected benzoin adducts. The reaction is general with respect to aryl, alkyl, and heterocyclic substrates with good to excellent yields and good to excellent enantioselectivities. Copyright
Preparation of Optically Active α-Acetoxyacylophenones via Enzyme Mediated Hydrolysis
Ohta, Hiromichi,Ikemoto, Mitsushi,Ii, Hiroyuki,Okamoto, Yasushi,Tsuchihashi, Gen-ichi
, p. 1169 - 1172 (2007/10/02)
Microorganisms that hydrolyzes α-acetoxyacylophenones were screened, and it was found that Pichia miso IAM 4682, a type culture belonging to yeast, gave the best results.The esterase of this microbe hydrolyzed (R)-acetates in a highly enantioselective manner.