2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones

The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.1 Introduction2 Background: Umpolung Strategies for Preparing Chiral Amines3 Background: 2-Azadienes4 Reductive Couplings of 2-Azadienes5 Fluoroarylations of gem-Difluoro-2-azadienes6 Summary and Outlook

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Essential oils (containing tertiary alcohols). Estimation of free alcohols content by determination of ester value after acetylation

10.3403/02332088u ◽

2015 ◽

Keyword(s):

Essential Oils ◽

Tertiary Alcohols

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Oxidations with chromium(VI) oxide. VI. Mechanism of oxidation of tertiary alcohols and their esters

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19580833 ◽

1958 ◽

Vol 23 (5) ◽

pp. 833-847 ◽

Cited By ~ 7

Author(s):

J. Roček

Keyword(s):

Tertiary Alcohols ◽

Chromium Vi ◽

Mechanism Of Oxidation

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Dual Roles of TBHP Enabled Regioselective Hydroetherification of (Trifluoromethyl)alkenes with Boronic Acids: Access to α-Trifluoromethyl β-Aryloxy Tertiary Alcohols

Synthesis ◽

10.1055/a-1481-2023 ◽

2021 ◽

Author(s):

Hengyuan Li ◽

Chuanle Zhu

Keyword(s):

Boronic Acids ◽

Dual Roles ◽

Tertiary Alcohols ◽

High Yields

The three-starting materials four-component reaction of (trifluoromethyl)alkenes, TBHP, and boronic acids is reported, delivering various useful α-trifluoromethyl-β-aryloxy tertiary alcohols in high yields and in an exclusively regioselective hydroetherification manner. TBHP serves as both the oxidants and the nucleophiles in this reaction, as well as the O-source of the products.

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Iminophosphorane-mediated regioselective umpolung alkylation reaction of α-iminoesters

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00596k ◽

2021 ◽

Author(s):

Yasushi Yoshida ◽

Mayu Kukita ◽

Kazuki Omori ◽

Takashi Mino ◽

Masami Sakamoto

Keyword(s):

Asymmetric Reactions ◽

Alkylation Reaction ◽

Chiral Amines ◽

Efficient Manner

Umpolung reactions of imines, especially the asymmetric reactions, have been extensively studied as they provide access to important chiral amines in an efficient manner. The reactions studied range from simple...

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