Bis(2-aminobenzoimidazole)-Organocatalyzed Asymmetric Alkylation of Activated Methylene Compounds with Benzylic and Allylic Alcohols

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Title: Bis(2-aminobenzoimidazole)-Organocatalyzed Asymmetric Alkylation of Activated Methylene Compounds with Benzylic and Allylic Alcohols
Authors: Trillo Alarcón, María Paz | Baeza, Alejandro | Nájera, Carmen
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT) | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Asymmetric catalysis | Alcohols | Organocatalysis | Carbocations | Alkylation
Knowledge Area: Química Orgánica
Issue Date: 2014
Publisher: Georg Thieme Verlag
Citation: Synthesis. 2014, 46(24): 3399-3414. doi:10.1055/s-0034-1378618
Abstract: The first organocatalyzed asymmetric alkylation of activated methylene compounds using benzylic and allylic alcohols as alkylating agents through dual hydrogen bond activation in an SN1-type reaction is reported. This green protocol employs a bis(2-aminobenzoimidazole) in combination with an achiral Brønsted acid as a bifunctional catalytic system and gives the alkylation products with moderate to good enantioselectivities. Although the scope of the reaction is limited, this methodology can be considered as complementary to existing metal-catalyzed processes. In addition, modest results were obtained in a first attempt to perform a metal-free asymmetric Tsuji–Trost reaction using allylic alcohols. Finally, the recovery and reusability of the organocatalyst is also achieved.
Sponsor: Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387 and Consolider Ingenio 2010, CSD2007-00006), FEDER, the Generalitat Valenciana (PROMETEO 2009/039) and the University of Alicante are gratefully acknowledged for financial support. A.B. would also like to thank University of Alicante (Project GRE12-03).
ISSN: 0039-7881 (Print) | 1437-210X (Online)
DOI: 10.1055/s-0034-1378618
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Georg Thieme Verlag Stuttgart · New York
Peer Review: si
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Appears in Collections:INV - CESO - Artículos de Revistas
INV - SINTAS - Artículos de Revistas
INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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