Reductive umpolung for asymmetric synthesis of chiral α-allenic alcohols

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

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

Synthesis of (R)-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl 4-Methylbenzenesulfonate

2014 ◽  
Vol 881-883 ◽  
pp. 465-468
Author(s):  
Dong Wang Liu ◽  
Lin Jun Tang ◽  
Li Ping Wang ◽  
Fei Fei Huang ◽  
Shuang Ping Huang ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Antidepressant Drug ◽  
Synthetic Route ◽  
New Generation

Venlafaxine (Figure 1) is the new generation antidepressant drug. A synthetic route to the asymmetric synthesis of (R)-venlafaxine through Evans Aldol protocol was designed. The key intermediate, (R)-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl) ethyl4-methylbenzenesulfonate was prepared from cyclohexanone.

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
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Synthetic Route

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.

ChemInform Abstract: Asymmetric Synthesis of Thioamido Selenides. A Simple Synthetic Route to Enantiopure Thiazolines.

ChemInform ◽  
2010 ◽  
Vol 33 (36) ◽  
pp. no-no
Author(s):  
Marcello Tiecco ◽  
Lorenzo Testaferri ◽  
Claudio Santi ◽  
Cristina Tomassini ◽  
Francesca Marini ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Synthetic Route

Diels–Alder addition of the fumarate and acrylate of S-methyl lactate to α-hydroxy orthoquinodimethanes

1989 ◽  
Vol 67 (4) ◽  
pp. 574-579 ◽  
Author(s):  
James L. Charlton ◽  
Guy L. Plourde ◽  
Kevin Koh ◽  
Anthony S. Secco
Keyword(s):  
Asymmetric Synthesis ◽  
Optical Purity ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Synthetic Route ◽  
Methyl Lactate ◽  
High Optical Purity ◽  
Single Diastereomer ◽  
Potential Use

The cycloaddition of α-hydroxy orthoquinodimethane, generated photochemically from 2-methylbenzaldehyde, to the fumarate and acrylate of S-methyl lactate has been found to give a single diastereomer with high asymmetric induction (>95% de). This reaction provides a new and versatile synthetic route to substituted tetralins of high optical purity. A trans stereochemistry between the vicinal hydroxyl and carboxylactyl groups has been established for these cycloadducts. This is in contrast to previous work where cis stereochemistry has always been found for major cycloadducts of α-hydroxy o-QDMs. The high asymmetric induction, unusual diastereoselectivity, and the potential use of these reactions in asymmetric synthesis are discussed. Keywords: o-quinodimethanes, Diels–Alder, asymmetric, cycloaddition, induction, diastereoselective.

Asymmetric synthesis of thioamido selenides. A simple synthetic route to enantiopure thiazolines

2002 ◽  
Vol 13 (4) ◽  
pp. 429-435 ◽  
Author(s):  
Marcello Tiecco ◽  
Lorenzo Testaferri ◽  
Claudio Santi ◽  
Cristina Tomassini ◽  
Francesca Marini ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Synthetic Route

scholarly journals Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether

Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 442-448
Author(s):  
Yujiro Hayashi ◽  
Shunsuke Toda
Keyword(s):  
Asymmetric Synthesis ◽  
Present Method ◽  
Michael Reaction ◽  
Side Chain ◽  
Silyl Ether ◽  
Synthetic Route

An efficient synthetic route to install chiral 1,3-dimethyl units through a double Michael reaction of crotonaldehyde and nitromethane catalyzed by diphenylprolinol silyl ether is developed. Either 1,3-syn- or 1,3-anti-dimethyl units are obtained selectively depending on the enantiomer of the diphenylprolinol silyl ether catalyst used. The side chain of pneumocandin B0 is synthesized enantioselectively by using the present method as a key step.

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