- Reversal diastereoselectivity between the organomagnesium and organolithium reagents on Chiral N-tert-butylsulfinylaldimines for the preparation of chiral amines
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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.
- Rajendiran, Chinnapillai,Nagarajan, Periyandi,Naidu,Dubey
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p. 2936 - 2942
(2014/11/08)
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- Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea
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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.
- Zhao, Qingyang,Wen, Jialin,Tan, Renchang,Huang, Kexuan,Metola, Pedro,Wang, Rui,Anslyn, Eric V.,Zhang, Xumu
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supporting information
p. 8467 - 8470
(2014/08/18)
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- One-pot synthesis of chiral nonracemic amines
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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.
- Roe, Caroline,Hobbs, Heather,Stockman, Robert A.
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experimental part
p. 9452 - 9459
(2012/01/06)
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- NOVEL URACIL COMPOUND HAVING INHIBITORY ACTIVITY ON HUMAN DEOXYURIDINE TRIPHOSPHATASE OR SALT THEREOF
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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.
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Page/Page column 52
(2011/04/18)
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- General one-pot method for the preparation of N-tert-butanesulfinylamine diastereomer mixtures as standards for stereoselectivity determinations
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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
- Brak, Katrien,Barrett, Kimberly T.,Ellman, Jonathan A.
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supporting information; experimental part
p. 3606 - 3608
(2009/09/06)
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- Enantioselective hydrogenation of N-H imines
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(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
- 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
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supporting information; experimental part
p. 9882 - 9883
(2009/12/06)
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- Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines
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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.
- Colyer, John T.,Andersen, Neil G.,Tedrow, Jason S.,Soukup, Troy S.,Faul, Margaret M.
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p. 6859 - 6862
(2007/10/03)
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- 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
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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
- Shi, Min,Lei, Zhi-Yu,Xu, Qin
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p. 2237 - 2242
(2007/10/03)
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- New, recoverable and highly effective sulfinyl chiral auxiliary
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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
- Kawecki, Robert
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p. 2827 - 2832
(2007/10/03)
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- Asymmetric synthesis of chiral amines by highly diastereoselective 1,2- additions of organometallic reagents to N-tert-butanesulfinyl imines
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High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert- butanesulfinyl kerimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6) delivers highly enantioenriched α-branched and α,α-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared.
- Cogan, Derek A.,Liu, Guangcheng,Ellman, Jonathan
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p. 8883 - 8904
(2007/10/03)
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- Chiral quaternary benzophenone hydrazonium salt derivatives; efficient chiral catalysts for the enantioselective phase-transfer alkylation of imines. Application to synthesis of chiral primary amines
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(2S)-1-Methyl-1-[N-(diphenylmethylene)-2-hydroxymethylpyrrolidine hydrazonium iodide I-a has been designed to catalyse the enantioselective phase-transfer alkylation of N-(diphenylmethylene) benzenemethanamine II. Although the weak acidic character of the latter, alkylations have been performed within reasonable reaction times. Optically active primary amines III a-e have been prepared in good chemical yields and up to 94% e.e. using 2-5 mol-% of the chiral catalyst only.
- Jamal Eddine,Cherqaoui
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p. 1225 - 1228
(2007/10/02)
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