Chemoenzymatic Resolution of β-Azidophenylethanols byCandida antarcticaand their Application for the Synthesis of Chiral Benzotriazoles

Abstract

99%). The enantiomerically enriched (R)-β-azidophenylethanols were subjected to cyclization reaction with 2-(trimethylsilyl)phenyl triflate and CsF producing chiral 1,2,3-benzotriazole compounds in good yields (75-86%) by a [3 + 2] cycloaddition, which involves the benzyne formation.]]>

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

“…This strategy smartly avoided the N 1/ N 2 regioselective problem in conventional alkylation reaction of benzotriazoles. Beside the aforementioned examples, this transition-metal-free aryne-azide [3 + 2] cycloaddition protocol turned out to be quite general and has found a broad spectrum of synthetic applications. − …”

Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa

“…Interesting examples for the preparation of enantiopure β-hydroxytriazoles derivatives by chemoenzymatic approaches can be surveyed in the literature, being ADHs the most employed enzymes in these multi-step procedures. In all these strategies, the stereocenter was defined before the CuAAC reaction [19][20][21][22][23][24]. In a recent report, a bioreduction of a β-ketotriazole was performed by a strain of Penicillium citrinum affording the corresponding (S)-β-hydroxytriazole in high enantiomeric excess (ee) values [25].…”

Reações aldólicas em biocatálise: o emprego de lipases como catalisadores e a aplicação do meio reacional de miniemulsão

“…(a) promiscuidade de condição (Rocha et al, 2013), (b) promiscuidade de substrato (Khare et al, 2009) e (c) promiscuidade de catálise (Branneby et al, 2003). ........................................... 6 Esquema 2 -Primeira reação aldólica assimétrica descrita na literatura (Li et al, 2008).…”

“…Esquema 1 -Exemplos dos diferentes tipos de promiscuidades enzimáticas da enzima CALB; (a) promiscuidade de condição (Rocha et al, 2013), (b) promiscuidade de substrato (Khare et al, 2009) e (c) promiscuidade de catálise (Branneby et al, 2003). (Yildiz et al, 2017).…”