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

R Settambolo, G Guazzelli, L Mengali, A Mandoli…

Index: Settambolo, Roberta; Guazzelli, Giuditta; Mengali, Lucia; Mandoli, Alessandro; Lazzaroni, Raffaello Tetrahedron Asymmetry, 2003 , vol. 14, # 17 p. 2491 - 2493

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Citation Number: 20

Abstract

(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-α- 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.