19068-33-8Relevant articles and documents
Reversal diastereoselectivity between the organomagnesium and organolithium reagents on Chiral N-tert-butylsulfinylaldimines for the preparation of chiral amines
Rajendiran, Chinnapillai,Nagarajan, Periyandi,Naidu,Dubey
, p. 2936 - 2942 (2014/11/08)
The asymmetric synthesis of both the enantiomer of chiral amines from the single chiral source of N-tert-butylsulfinylaldimines (3) by simply changing the organometallic reagents through diastereoselective addition. An efficient enantioselective synthesis of chiral amines including (S)-3-methyl-1-(2- piperidin-1-yl-phenyl)butyl amine (6a), a key intermediate to prepare antidiabetic drug repaglinide (1), is reported.
Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea
Zhao, Qingyang,Wen, Jialin,Tan, Renchang,Huang, Kexuan,Metola, Pedro,Wang, Rui,Anslyn, Eric V.,Zhang, Xumu
supporting information, p. 8467 - 8470 (2014/08/18)
Asymmetric hydrogenation of unprotected NH imines catalyzed by rhodium/bis(phosphine)-thiourea provided chiral amines with up to 97% yield and 95% ee. 1HNMR studies, coupled with control experiments, implied that catalytic chloride-bound intermediates were involved in the mechanism through a dual hydrogen-bonding interaction. Deuteration experiments proved that the hydrogenation proceeded through a pathway consistent with an imine.
One-pot synthesis of chiral nonracemic amines
Roe, Caroline,Hobbs, Heather,Stockman, Robert A.
experimental part, p. 9452 - 9459 (2012/01/06)
One-pot five-component reactions of oxathiazolidine-S-oxides with mesitylmagnesium bromide, lithium bis(trimethylsilyl)amide, aldehydes and Grignard reagents afford chiral nonracemic amines or sulfinamides in good yields and high stereoselectivities.
NOVEL URACIL COMPOUND HAVING INHIBITORY ACTIVITY ON HUMAN DEOXYURIDINE TRIPHOSPHATASE OR SALT THEREOF
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Page/Page column 52, (2011/04/18)
Provided is a uracil compound or a salt thereof, which has potent human dUTPase inhibitory activity and is useful as, for example, an antitumor drug. A uracil compound represented by the general formula (I) or a salt thereof: wherein n represents an integer of 1 to 3; X represents a bond, an oxygen atom, a sulfur atom, or the like; Y represents a linear or branched alkylene group having 1 to 8 carbon atoms, or the like; and Z represents -SO2NR1R2 or -NR3SO2-R4, wherein R1 and R2 each represent an alkyl group having 1 to 6 carbon atoms, an aralkyl group which is optionally substituted, or the like; R3 represents an alkyl group having 1 to 6 carbon atoms, or the like; and R4 represents an aromatic hydrocarbon group, an unsaturated heterocyclic group, or the like.
Enantioselective hydrogenation of N-H imines
Hou, Guohua,Gosselin, Francis,Li, Wei,McWilliams, J. Christopher,Sun, Yongkui,Weisel, Mark,O'Shea, Paul D.,Chen, Cheng-Yi,Davies, Ian W.,Zhang, Xumu
supporting information; experimental part, p. 9882 - 9883 (2009/12/06)
(Figure Presented) N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v usi
General one-pot method for the preparation of N-tert-butanesulfinylamine diastereomer mixtures as standards for stereoselectivity determinations
Brak, Katrien,Barrett, Kimberly T.,Ellman, Jonathan A.
supporting information; experimental part, p. 3606 - 3608 (2009/09/06)
The one-pot preparation of N-sulfinylamine diastereomers proceeds in excellent yields (84-98%) for a diverse set of N-sulfinyl imine addition products. The method is operationally simple and extractive isolation provides analytically pure mixtures of dias
Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines
Colyer, John T.,Andersen, Neil G.,Tedrow, Jason S.,Soukup, Troy S.,Faul, Margaret M.
, p. 6859 - 6862 (2007/10/03)
A variety of N-tert-butanesulfinyl imines were reduced with NaBH 4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.
Asymmetric addition of diethylzinc to diphenylphosphinoyl-imines catalyzed by copper(II) trifluoromethanesulfonate-chiral (2′-ethylamino-[1,1′] binaphthalenyl-2-yl)-thiophosphoramidic acid O,O′-diaryl ester ligands
Shi, Min,Lei, Zhi-Yu,Xu, Qin
, p. 2237 - 2242 (2007/10/03)
The chiral binaphthylthiophosphoramide L1 prepared from the reaction of O,O-diphenyl chlorothiophosphate with (R)-(+)-N-ethyl-1,1′-binaphthyl-2, 2′-diamine was used as a catalytic chiral ligand in the copper(II) trifluoromethanesulfonate-promoted asymmetr
New, recoverable and highly effective sulfinyl chiral auxiliary
Kawecki, Robert
, p. 2827 - 2832 (2007/10/03)
A facile synthesis of a bicyclic 8-menthylsulfinate is described. The reaction of this sultine with organometallic compounds leads to γ-hydroxysulfoxides, while the reaction with lithium amide affords 8-menthylsulfinamide. The chiral efficiency of the 8-m