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ChemInform Abstract: 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
2010
Weight
32 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

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 diastereoselectivity of this reaction depends on the bulkiness of the amino acid chain. Treatment of the esters with H 2 SO 4 leads to α-methylene lactones which are ideal synthetic synthons. -(STEURER,

📜 SIMILAR VOLUMES

Aminoalkyl-Substituted α-Methylene-γ-but
Aminoalkyl-Substituted α-Methylene-γ-butyrolactones from α-Amino Acids Using an Indium-Mediated Barbier Allyl Addition
✍ Steffen Steurer; Joachim Podlech 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 398 KB

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 wit