Asymmetric synthesis of 8-aminoindolizidine from chiral 2-pyrroleimines

VG Albano, A Gualandi, M Monari…

Index: Albano, Vincenzo Giulio; Gualandi, Andrea; Monari, Magda; Savoia, Diego Journal of Organic Chemistry, 2008 , vol. 73, # 21 p. 8376 - 8381

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Citation Number: 26

Abstract

1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts, to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerization of the 1-pyrrole substituent. Transformation of the 2-amino alcohol moiety to an oxazolidinone, or its cleavage and subsequent N-protection, followed by ring-closing metathesis of the ...