scholarly journals Practical and Asymmetric Synthesis of Apremilast Using Ellman’s Sulfinamide as a Chiral Auxiliary

Molbank ◽  
10.3390/m1275 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1275
Author(s):  
Bofei Wang ◽  
Fangrui Zhong

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and with 95.5% ee.

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.


2008 ◽  
Vol 2008 (35) ◽  
pp. 5915-5921 ◽  
Author(s):  
Ellen M. Santangelo ◽  
Ilme Liblikas ◽  
Anoma Mudalige ◽  
Karl W. Törnroos ◽  
Per-Ola Norrby ◽  
...  

2013 ◽  
Vol 54 (41) ◽  
pp. 5555-5557 ◽  
Author(s):  
Ashutosh Pal ◽  
Zhenghong Peng ◽  
Paul T. Schuber ◽  
Basvoju A. Bhanu Prasad ◽  
William G. Bornmann

2020 ◽  
Vol 56 (54) ◽  
pp. 7471-7474
Author(s):  
Yui Kondo ◽  
Kazunori Nagao ◽  
Hirohisa Ohmiya

Copper-catalyzed reductive umpolung provides a new synthetic route to chiral α-allenic alcohols.


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