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Aminoalkyl-Substituted α-Methylene-γ-butyrolactones from α-Amino Acids Using an Indium-Mediated Barbier Allyl Addition

✍ Scribed by Steffen Steurer; Joachim Podlech

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
398 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

The indium-mediated reaction of Z-protected α-amino transformation of the amino aldehydes. Acid-catalyzed esterification (H 2 SO 4 in Et 2 O) led to α-methylene-γaldehydes 1-6 with 2-(bromomethyl)acrylates 8/9 in aqueous solvents has been investigated. The preference for the butyrolactones 17-22 with yields ranging from 89 to 97%.

The configurations of all diastereoisomers were established formation of syn-configured homoallyl alcohols 10-16 (diastereoselectivities ranging from 2:1 to 32:1, yields 68-by five X-ray crystallographic analyses and by comparision of the NMR spectra. 93%) may be explained by a chelate-controlled reaction. No racemization occurred during the preparation and als employed in the Barbier reaction (Zn, 17,

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ChemInform Abstract: Aminoalkyl-Substitu
ChemInform Abstract: Aminoalkyl-Substituted α-Methylene-γ-butyrolactones from α-Amino Acids Using an Indium-Mediated Barbier Allyl Addition.
✍ Steffen Steurer; Joachim Podlech 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

Aminoalkyl-Substituted α-Methylene-γ-butyrolactones from α-Amino Acids Using an Indium-Mediated Barbier Allyl Addition. α-Amino aldehydes, prepared from α-amino acids, can be cleanly transformed into esters of type (III) in high yields and without racemization by In-induced Barbier reaction. The di