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The proline-catalyzed double Mannich reaction of acetaldehyde with N-Boc imines.
Angew Chem Int Ed Engl. 2009; 48(11):1978-80.AC

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-C(2)-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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Publisher Full Text (DOI)

Authors+Show Affiliations

Chandler C
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
Galzerano P
No affiliation info available
Michrowska A
No affiliation info available
List B
No affiliation info available

MeSH

AcetaldehydeCatalysisIminesProlineStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19199308

Citation

Chandler, Carley, et al. "The Proline-catalyzed Double Mannich Reaction of Acetaldehyde With N-Boc Imines." Angewandte Chemie (International Ed. in English), vol. 48, no. 11, 2009, pp. 1978-80.
Chandler C, Galzerano P, Michrowska A, et al. The proline-catalyzed double Mannich reaction of acetaldehyde with N-Boc imines. Angew Chem Int Ed Engl. 2009;48(11):1978-80.
Chandler, C., Galzerano, P., Michrowska, A., & List, B. (2009). The proline-catalyzed double Mannich reaction of acetaldehyde with N-Boc imines. Angewandte Chemie (International Ed. in English), 48(11), 1978-80. https://doi.org/10.1002/anie.200806049
Chandler C, et al. The Proline-catalyzed Double Mannich Reaction of Acetaldehyde With N-Boc Imines. Angew Chem Int Ed Engl. 2009;48(11):1978-80. PubMed PMID: 19199308.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The proline-catalyzed double Mannich reaction of acetaldehyde with N-Boc imines. AU - Chandler,Carley, AU - Galzerano,Patrizia, AU - Michrowska,Anna, AU - List,Benjamin, PY - 2009/2/10/entrez PY - 2009/2/10/pubmed PY - 2009/4/29/medline SP - 1978 EP - 80 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 48 IS - 11 N2 - 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-C(2)-symmetric diastereomer and the corresponding meso compound can be prepared. Cross double Mannich reactions of acetaldehyde with two different imines are also demonstrated. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/19199308/The_proline_catalyzed_double_Mannich_reaction_of_acetaldehyde_with_N_Boc_imines_ L2 - https://doi.org/10.1002/anie.200806049 DB - PRIME DP - Unbound Medicine ER -