Enantioselective Synthesis of syn- and anti-1,3-Aminoalcohols via β-Aminoketones and Subsequent Reduction/Dynamic Kinetic Asymmetric Transformation

β-Aminoketones obtained from imines in an organocatalytic Mannich reaction were transformed to enantio- and diastereomerically pure 1,3-aminoalcohols with two stereogenic centers via a combined reduction/dynamic kinetic asymmetric transformation. Both syn and anti diastereomers were obtained in high...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-11, Vol.132 (43), p.15182-15184
Main Authors: Millet, Renaud, Träff, Annika M, Petrus, Michiel L, Bäckvall, Jan-E
Format: Article
Language:English
Subjects:
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Biocatalysis
Fungal Proteins
Ketones - chemistry
Kinetics
Lipase - metabolism
Organometallic Compounds - chemistry
Oxidation-Reduction
Stereoisomerism
Substrate Specificity
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Summary:β-Aminoketones obtained from imines in an organocatalytic Mannich reaction were transformed to enantio- and diastereomerically pure 1,3-aminoalcohols with two stereogenic centers via a combined reduction/dynamic kinetic asymmetric transformation. Both syn and anti diastereomers were obtained in high yield, dr, and ee.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja107857v