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A new class of optically active pyrrole derivatives: (3R)-3-(pyrrol-1-yl)alk-1-enes from d-α-aminoacids

✍ Scribed by Roberta Settambolo; Giuditta Guazzelli; Lucia Mengali; Alessandro Mandoli; Raffaello Lazzaroni

Book ID: 104359997
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 190 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00524-x

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✦ Synopsis

3R)-3-(Pyrrol-1-yl)but-1-ene 4a, (3R)-4-methyl-3-(pyrrol-1-yl)pent-1-ene 4b, (3R)-3-(pyrrol-1-yl)hex-1-ene 4c in high enantiomeric excess (>92%) were prepared starting from D-a-amino acids. The crucial steps in the synthesis, reduction (DIBAH) of the corresponding pyrrolylesters to the corresponding pyrrolylaldehydes followed by Wittig olefination proceeded without compromising the stereochemical integrity.

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