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Keywords = O-acyl cyanohydrins

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89 pages, 6033 KiB  
Review
Recent Advances on O-Ethoxycarbonyl and O-Acyl Protected Cyanohydrins
by Héctor Manuel Torres Domínguez, Luis Mauricio Hernández Villaverde and Ronan Le Lagadec
Molecules 2021, 26(15), 4691; https://doi.org/10.3390/molecules26154691 - 3 Aug 2021
Cited by 1 | Viewed by 3335
Abstract
Ethoxycarbonyl cyanohydrins and O-acyl cyanohydrins are examples of O-protected cyanohydrins in which the protecting group presents an electrophilic center, contributing to additional reaction pathways. The first section of this review describes recent advances on the synthesis of O-ethoxycarbonyl and O [...] Read more.
Ethoxycarbonyl cyanohydrins and O-acyl cyanohydrins are examples of O-protected cyanohydrins in which the protecting group presents an electrophilic center, contributing to additional reaction pathways. The first section of this review describes recent advances on the synthesis of O-ethoxycarbonyl and O-acyl protected cyanohydrins. Reactions using KCN or alkyl cyanoformates as the cyanide ion source are described, as well as organic and transition metal catalysis used in their preparation, including asymmetric cyanation. In a second part, transformations, and synthetic applications of O-ethoxycarbonyl/acyl cyanohydrins are presented. A variety of structures has been obtained starting from such protected cyanohydrins and, in particular, the synthesis of oxazoles, 1,4-diketones, 1,3-diketones, 2-vinyl-2-cyclopentenones through various methods are discussed. Full article
(This article belongs to the Special Issue Cyanide Chemistry)
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17 pages, 2304 KiB  
Article
Multi-Catalytic Route for the Synthesis of (S)-Tembamide
by Laura Leemans, Marc D. Walter, Frank Hollmann, Anett Schallmey and Luuk M. van Langen
Catalysts 2019, 9(10), 822; https://doi.org/10.3390/catal9100822 - 29 Sep 2019
Cited by 3 | Viewed by 4304
Abstract
Enantiopure β-amino alcohols constitute one of the most significant building blocks for the synthesis of active pharmaceutical ingredients. Despite the availability of a range of chiral β-amino alcohols from a chiral pool, there is a growing demand for new enantioselective synthetic routes to [...] Read more.
Enantiopure β-amino alcohols constitute one of the most significant building blocks for the synthesis of active pharmaceutical ingredients. Despite the availability of a range of chiral β-amino alcohols from a chiral pool, there is a growing demand for new enantioselective synthetic routes to vicinal amino alcohols and their derivatives. In the present study, an asymmetric 2-step catalytic route that converts 4-anisaldehyde into a β-amino alcohol derivative, (S)-tembamide, with excellent enantiopurity (98% enantiomeric excess) has been developed. The recently published initial step consists in a concurrent biocatalytic cascade for the synthesis of (S)-4-methoxymandelonitrile benzoate. The O-benzoyl cyanohydrin is then converted to (S)-tembamide in a hydrogenation reaction catalyzed by Raney Ni. To achieve hydrogenation of the nitrile moiety with highest chemoselectivity and enantioretention, various parameters such as nature of the catalyst, reaction temperature and hydrogen pressure were studied. The reported strategy might be transferrable to the synthesis of other N-acyl-β-amino alcohols. Full article
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