Tetrahedron

Preparation of both enantiomers of 1-allyl-1, 2, 3, 4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from l-proline

T Itoh, Y Matsuya, Y Enomoto, A Ohsawa

Index: Itoh, Takashi; Matsuya, Yuji; Enomoto, Yasuko; Ohsawa, Akio Tetrahedron, 2001 , vol. 57, # 34 p. 7277 - 7289

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Citation Number: 19

Abstract

β-Carboline, which had an acyl group derived from l-proline at the 9-position, reacted with allyltributyltin and 2, 2, 2-trichloroethyl chloroformate to afford an 1-allyl-1, 2-dihydro-β- carboline derivative in a diastereoselective manner. The chiral acyl group at N-9 was readily eliminated by aqueous alkali to give a corresponding carboxylic acid. The formed 1-allyl-1, 2- dihydro-β-carboline was transformed via two reduction steps to 1-allyl-1, 2, 3, 4-tetrahydro ...