131350-15-7Relevant academic research and scientific papers
Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics
Hogan, Philip C.,Chen, Chi-Li,Mulvihill, Kristen M.,Lawrence, Jonathan F.,Moorhead, Eric,Rickmeier, Jens,Myers, Andrew G.
, p. 318 - 325 (2018/03/21)
Key building blocks for the production of fully synthetic macrolides have been scaled-up in first time pilot plant and kilo-lab campaigns. These building blocks have supported the discovery of new macrolide antibiotics as well as ongoing preclinical studies.
Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis
Morales, Marvin R.,Mellem, Kevin T.,Myers, Andrew G.
supporting information; experimental part, p. 4568 - 4571 (2012/06/30)
Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright
Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols
Hirayama, Lacie C.,Gamsey, Soya,Knueppel, Daniel,Steiner, Derek,Delatorre, Kelly,Singaram, Bakthan
, p. 2315 - 2318 (2007/10/03)
We report a general method for the indium-mediated Barbier-type enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1S,2R)-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary. Using only two equivalents of allyl bromide, excellent yields and very good to excellent enantioselectivities are obtained. To our knowledge, the enantioselectivities reported herein are the highest obtained for indium-promoted allylations of carbonyl compounds.
Asymmetric hydrogenation of chiral vinyloxazaborolidines under ambient conditions
Gamsey, Soya,DeLaTorre, Kelly,Singaram, Bakthan
, p. 711 - 715 (2007/10/03)
Novel homochiral vinyloxazaborolidines have been synthesized and subsequently hydrogenated using palladium on carbon under ambient conditions to produce, after oxidation of the boronate group, enantiomerically enriched secondary alcohols (up to 20% ee). H
Enzyme-Catalyzed Reactions, 8. - Stereoselective Synthesis of 2-Amino Alcohols from (R)- and (S)-Cyanohydrins
Effenberger, Franz,Gutterer, Beate,Ziegler, Thomas
, p. 269 - 273 (2007/10/02)
erythro-2-Amino alcohols (1R,2S)- and (1S,2R)-4 may be synthesized stereoselectively by addition of Grignard compounds to cyanohydrins (R)-, (S)-1 and their O-trimethylsilyl derivatives 3, respectively, followed by hydrogenation.The threo-2-amino alcohols (1S,2S)- and (1R,2R)-4 are easily accessible by inversion at C-1 of the (1R,2S) and (1S,2R) compounds.
