Enantioselective Titanium(III)‐Catalyzed Reductive Cyclization of Ketonitriles

Streuff, Jan; Feurer, Markus; Bichovski, Plamen; Frey, Georg; Gellrich, Urs

doi:10.1002/anie.201204469

Cited by 119 publications

(56 citation statements)

References 53 publications

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“…Thet itanocenes used so far in enantioselective redox chemistry are C 2 -symmetrical (Kagans complex for epoxide opening [13] and Brintzingers complex for ketyl radical additions to nitriles). [14] Our results show that this is not an essential condition.…”

Section: Methodsmentioning

confidence: 56%

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

et al. 2015

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Two new catalytic systems for hydrogen-atom transfer (HAT) catalysis involving the N-H bonds of titanocene(III) complexes with pendant amide ligands are reported. In a monometallic system, a bifunctional catalyst for radical generation and reduction through HAT catalysis depending on the coordination of the amide ligand is employed. The pendant amide ligand is used to activate Crabtree's catalyst to yield an efficient bimetallic system for radical generation and HAT catalysis.

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Section: Methodsmentioning

confidence: 56%

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

et al. 2015

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“…Neither did a slight modification of this combination (Table , entry 2). The potential titanocene‐regenerating system summarized in Table entry 3, was not capable of providing more than 30 % yield of the desired homopropargylic alcohol 2 . After assaying the combination reported in Table entry 4, only the starting material ( 1 ) was obtained, suggesting that it decomposes the CpTiCl 2 catalyst.…”

Section: Resultsmentioning

confidence: 99%

CpTiCl₂, an Improved Titanocene(III) Catalyst in Organic Synthesis

et al. 2018

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Preparation, EPR analysis, and advantages in green organic chemistry of CpTiCl2, an improved single‐electron transfer catalyst, are reported. Under mild conditions, this organometallic complex provides excellent yields of homoallylic and homopropargylic alcohols in Barbier‐type allylation and propargylation reactions. Moreover, in the presence of a bidentate BOX ligand, Barbier‐type cyclization reactions catalyzed by CpTiCl2 can be carried out in an enantioselective manner.

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“…The enantioselective Ti‐catalyzed reductive cyclization of ketonitrile 47 was reported by Streuff's group (Scheme ) . Employing a combination of chiral titanocene catalyst ent ‐ 45 (10 mol %) and Zn (2 equiv), the product 48 was obtained in 88 % yield and 91 % ee .…”

Section: Chiral Metallic Reagent‐mediated Reactionsmentioning

confidence: 99%

Progress in Enantioselective Radical Cyclizations

Miyabe

Kawashima

Yoshioka

et al. 2017

Chemistry A European J

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The control of stereoselectivity in radical reactions is of great importance to organic synthesis. Hence, new concepts and strategies for controlling stereochemistry of radical reactions are emerging continuously. This Review highlights the recent remarkable progress in enantioselective radical cyclization reactions. Initially, the chiral Lewis acid-catalyzed method became a field of central importance for enantioselective radical cyclizations. In recent years, significant progress has been made in enantioselective organocatalysis. In contrast to intermolecular reactions, the successful examples for enantioselective radical cyclizations are still limited. In this Review, the radical cyclizations controlled by chiral Lewis acids, chiral metallic reagents, chiral imidazolidinone catalysts, chiral non-covalent organocatalysts, and chiral thiols are summarized.

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Enantioselective Titanium(III)‐Catalyzed Reductive Cyclization of Ketonitriles

Cited by 119 publications

References 53 publications

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

CpTiCl₂, an Improved Titanocene(III) Catalyst in Organic Synthesis

Progress in Enantioselective Radical Cyclizations

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Enantioselective Titanium(III)‐Catalyzed Reductive Cyclization of Ketonitriles

Cited by 119 publications

References 53 publications

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

CpTiCl2, an Improved Titanocene(III) Catalyst in Organic Synthesis

Progress in Enantioselective Radical Cyclizations

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Product

Resources

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CpTiCl₂, an Improved Titanocene(III) Catalyst in Organic Synthesis