Literature DB >> 16117531

A highly efficient and direct approach for synthesis of enantiopure beta-amino alcohols by reductive cross-coupling of chiral N-tert-butanesulfinyl imines with aldehydes.

Yu-Wu Zhong1, Yi-Zhou Dong, Kai Fang, Kenji Izumi, Ming-Hua Xu, Guo-Qiang Lin.   

Abstract

A highly efficient and practical approach for the synthesis of optically pure beta-amino alcohols by the SmI2-induced reductive cross-coupling of chiral N-tert-butanesulfinyl imines with aldehydes was developed. This method allows the preparation of a broad range of chiral beta-amino alcohols, including functionalized ones under mild conditions. It provides a straightforward access to enantiopure beta-amino alcohols that are widely applicable in asymmetric synthesis.

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Year:  2005        PMID: 16117531     DOI: 10.1021/ja054401w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Highly diastereoselective and general synthesis of primary β-fluoroamines.

Authors:  Michael L Schulte; Craig W Lindsley
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

2.  A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

Authors:  Shengyang Ni; Alberto F Garrido-Castro; Rohan R Merchant; Justine N de Gruyter; Daniel C Schmitt; James J Mousseau; Gary M Gallego; Shouliang Yang; Michael R Collins; Jennifer X Qiao; Kap-Sun Yeung; David R Langley; Michael A Poss; Paul M Scola; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-15       Impact factor: 15.336

3.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

4.  Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-epi-Acetaminic Acid, and 8-epi-Legionaminic Acid Glycosyl Donors from N-Acetylneuraminic Acid by Side Chain Exchange.

Authors:  Sameera Siyabalapitiya Arachchige; David Crich
Journal:  Org Lett       Date:  2022-04-14       Impact factor: 6.072

5.  Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol.

Authors:  Ali Dai; Yuanqin Huang; Lijiao Yu; Zhiguo Zheng; Jian Wu
Journal:  BMC Chem       Date:  2022-05-17

6.  Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis.

Authors:  Sean M Rafferty; Joy E Rutherford; Lumin Zhang; Lu Wang; David A Nagib
Journal:  J Am Chem Soc       Date:  2021-04-08       Impact factor: 15.419

7.  Crystal structures of (R S)-N-[(1R,2S)-2-benz-yloxy-1-(2,6-di-methyl-phen-yl)prop-yl]-2-methyl-propane-2-sulfinamide and (R S)-N-[(1S,2R)-2-benz-yloxy-1-(2,4,6-tri-methyl-phen-yl)prop-yl]-2-methyl-propane-2-sulfinamide: two related protected 1,2-amino alcohols.

Authors:  Matthew R Carbone; Garrick A Centola; Adam Haas; Kevin P McClelland; Michael D Moskowitz; Angelo M Verderame; Mikael S Olezeski; Louis J Papa; Stephanie C M Dorn; William W Brennessel; Daniel J Weix
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-10-24

8.  Dual catalysis for enantioselective convergent synthesis of enantiopure vicinal amino alcohols.

Authors:  Chen-Xi Ye; Yared Yohannes Melcamu; Heng-Hui Li; Jiang-Tao Cheng; Tian-Tian Zhang; Yuan-Ping Ruan; Xiao Zheng; Xin Lu; Pei-Qiang Huang
Journal:  Nat Commun       Date:  2018-01-29       Impact factor: 14.919

Review 9.  Synthesis of Nitrogen Heterocycles Using Samarium(II) Iodide.

Authors:  Shicheng Shi; Michal Szostak
Journal:  Molecules       Date:  2017-11-21       Impact factor: 4.411

  9 in total

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