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Abstract

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Paper | Special issue | Vol 88, No. 2, 2014, pp. 1477 - 1489
Published online: 24th October, 2013
DOI: 10.3987/COM-13-S(S)116
Bi(OTf)3 as a Dual Role Catalyst. Synthesis of Substituted Morpholine Derivatives via Catalytic O-Allylation

Ryuji Hayashi, Jin-A Park, and Gregory R. Cook*

*Department of Chemistry and Biochemistry, North Dakota State University, Fargo, North Dakota 58108, U.S.A.

Abstract

The diastereoselective synthesis of cis-1,4-disubstituted morpholines has been accomplished in good to excellent yields via Bi(OTf)3 catalyzed ring-closing O-allylation under mild conditions without the need for added base. The bismuth Lewis acid catalyst appeared to play two roles; the mild deprotection of a silyl ether and the Lewis acid activation of an allylic halide for mild nucelophilic cyclization. Substituted morpholines were obtained with diastereoselectivity ranging from 2:1 to >99:1.

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