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  The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines

Chandler, C., Galzerano, P., Michrowska, A., & List, B. (2009). The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines. Angewandte Chemie International Edition, 48(11), 1978-1980. doi:10.1002/anie.200806049.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000F-8F5B-6 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-47FF-A
Genre: Journal Article

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 Creators:
Chandler, Carley1, Author           
Galzerano, Patrizia1, Author           
Michrowska, Anna1, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: aldehydes; diastereoselectivity; enantioselectivity; Mannich reaction; organocatalysis
 Abstract: Double‐cross: Proline catalyzes the double Mannich reaction of acetaldehyde with N‐Boc imines in excellent yields (up to 99 %; Boc=tert‐butoxycarbonyl) and close to perfect diastereo‐ and enantioselectivities. Depending on the choice of catalysts, both the chiral, pseudo‐C2‐symmetric diastereomer and the corresponding meso compound can be prepared. Cross double Mannich reactions of acetaldehyde with two different imines are also demonstrated.

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Language(s): eng - English
 Dates: 2008-12-122009-02-232009-03-02
 Publication Status: Issued
 Pages: 3
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.200806049
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 48 (11) Sequence Number: - Start / End Page: 1978 - 1980 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851