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2008 1
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Page 1
Asymmetric Synthesis of Pyrrolidines via Oxetane Desymmetrization.
Zhang R, Sun M, Yan Q, Lin X, Li X, Fang X, Sung HHY, Williams ID, Sun J. Zhang R, et al. Org Lett. 2022 Apr 1;24(12):2359-2364. doi: 10.1021/acs.orglett.2c00564. Epub 2022 Mar 24. Org Lett. 2022. PMID: 35322664
Herein we report two efficient protocols by means of oxetane desymmetrization, featuring the use of a readily available tert-butylsulfinamide chiral auxiliary and a catalytic system with chiral phosphoric acid as the source of chirality, respectively....
Herein we report two efficient protocols by means of oxetane desymmetrization, featuring the use of a readily available tert-butyl …
The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis.
Bauer RA, DiBlasi CM, Tan DS. Bauer RA, et al. Org Lett. 2010 May 7;12(9):2084-7. doi: 10.1021/ol100574y. Org Lett. 2010. PMID: 20356070 Free PMC article.
A unified synthetic approach to diverse polycyclic scaffolds has been developed using transition-metal-mediated cycloaddition and cyclization reactions of enynes and diynes. The tert-butylsulfinamide group has been identified as a particularly versatile lynchpin in …
A unified synthetic approach to diverse polycyclic scaffolds has been developed using transition-metal-mediated cycloaddition and cyclizatio …
Asymmetric Transfer Hydrogenation of N-Unprotected Indoles with Ammonia Borane.
Zhao W, Zhang Z, Feng X, Yang J, Du H. Zhao W, et al. Org Lett. 2020 Aug 7;22(15):5850-5854. doi: 10.1021/acs.orglett.0c01930. Epub 2020 Jul 14. Org Lett. 2020. PMID: 32663407
A metal-free asymmetric transfer hydrogenation of unprotected indoles was successfully realized using a catalyst derived from HB(C(6)F(5))(2) and (S)-tert-butylsulfinamide with ammonia borane as a hydrogen source. ...
A metal-free asymmetric transfer hydrogenation of unprotected indoles was successfully realized using a catalyst derived from HB(C(6)F(5))(2 …
Asymmetric Transfer Hydrogenations of 2,3-Disubstituted Quinoxalines with Ammonia Borane.
Li S, Meng W, Du H. Li S, et al. Org Lett. 2017 May 19;19(10):2604-2606. doi: 10.1021/acs.orglett.7b00935. Epub 2017 May 1. Org Lett. 2017. PMID: 28459591
An asymmetric transfer hydrogenation of 2,3-disubstituted quinoxalines using a chiral frustrated Lewis pair of Piers' borane and (R)-tert-butylsulfinamide as the catalyst with ammonia borane as the hydrogen source has been successfully realized. ...
An asymmetric transfer hydrogenation of 2,3-disubstituted quinoxalines using a chiral frustrated Lewis pair of Piers' borane and (R)-tert …
Frustrated Lewis Pairs Catalyzed Asymmetric Metal-Free Hydrogenations and Hydrosilylations.
Meng W, Feng X, Du H. Meng W, et al. Acc Chem Res. 2018 Jan 16;51(1):191-201. doi: 10.1021/acs.accounts.7b00530. Epub 2017 Dec 15. Acc Chem Res. 2018. PMID: 29243918
Moreover, asymmetric transfer hydrogenations of imines and quinoxalines with ammonia borane as the hydrogen source have been achieved with frustrated Lewis pair of Piers' borane and (R)-tert-butylsulfinamide as the catalyst. Mechanistic studies have suggested that t …
Moreover, asymmetric transfer hydrogenations of imines and quinoxalines with ammonia borane as the hydrogen source have been achieved with f …
Synthesis of β,γ-dihydroxyhomotyrosines by a tandem Petasis-asymmetric dihydroxylation approach.
Churches QI, White JM, Hutton CA. Churches QI, et al. Org Lett. 2011 Jun 3;13(11):2900-3. doi: 10.1021/ol200917s. Epub 2011 May 11. Org Lett. 2011. PMID: 21561144
Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the 'amine' component, proceed with high stereoselectivity to produce beta,gamma-dehydrohomoarylalanine derivatives. ...
Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the 'amine' comp …
Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: synthesis, pharmacological evaluation and mechanistic studies.
Llabrés S, García-Ratés S, Cristóbal-Lecina E, Riera A, Borrell JI, Camarasa J, Pubill D, Luque FJ, Escubedo E. Llabrés S, et al. Eur J Med Chem. 2014 Jun 23;81:35-46. doi: 10.1016/j.ejmech.2014.04.044. Epub 2014 May 2. Eur J Med Chem. 2014. PMID: 24942641 Free article.
To this end, we report a novel simple, yet highly efficient enantioselective synthesis of the MDMA enantiomers, in which the key step is the diastereoselective reduction of imides derived from optically pure tert-butylsulfinamide. The enantioselective binding to the …
To this end, we report a novel simple, yet highly efficient enantioselective synthesis of the MDMA enantiomers, in which the key step is the …
A Frustrated Lewis Pair Catalyzed Asymmetric Transfer Hydrogenation of Imines Using Ammonia Borane.
Li S, Li G, Meng W, Du H. Li S, et al. J Am Chem Soc. 2016 Oct 5;138(39):12956-12962. doi: 10.1021/jacs.6b07245. Epub 2016 Sep 21. J Am Chem Soc. 2016. PMID: 27607840
Inspired by the zwitterion species generated from the splitting of H(2) by frustrated Lewis pairs, we put forward a novel frustrated Lewis pair by the combination of H(delta-) and H(delta+) incorporated Lewis acid and base together. Piers' borane and chiral tert-butylsu …
Inspired by the zwitterion species generated from the splitting of H(2) by frustrated Lewis pairs, we put forward a novel frustrated Lewis p …
Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an alpha-chloroimine.
Hodgson DM, Kloesges J, Evans B. Hodgson DM, et al. Org Lett. 2008 Jul 3;10(13):2781-3. doi: 10.1021/ol800961a. Epub 2008 Jun 4. Org Lett. 2008. PMID: 18522390
Addition of N-(2-chloroethylidene)- tert-butylsulfinamide to organocerium reagents in DMPU/THF (1:10) at -78 degrees C followed by warming to 25 degrees C provides terminal N-tert-butylsulfinyl aziridines in good yields (63-92%, nine examples) and diastereomeric rat …
Addition of N-(2-chloroethylidene)- tert-butylsulfinamide to organocerium reagents in DMPU/THF (1:10) at -78 degrees C followe …
15 results