Comparison of the allylation reactions of aldehydes using allylstannanes with boron trifluoride etherate and boron trichloride

D Marton, G Tagliavini, M Zordan, JL Wardell

Index: Marton, Daniele; Tagliavini, Giuseppe; Zordan, Michele; Wardell, James L. Journal of Organometallic Chemistry, 1990 , vol. 390, # 2 p. 127 - 138

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Citation Number: 12

Abstract

Abstract Reactions between allylstannanes, R 2 CH= CHCHR 1 SnBu 3 (R 1= R 2= H (4); R 1= H, R 2= Me (5); R 1 R 2=(CH 2) 3 (6)) and aldehydes, RCHO (eg R= Et) in the presence of BF 3· OEt 2 in CH 2 Cl 2 at− 78 C produce stereoselectively erythro-RCH (OH) CHR 2 CH= CHR 1 (with one equivalent RCHO) and 4-OH-3-R 1-5-R 2-2, 6-R 2-tetrahydropyrans (with an excess of RCHO). In contrast, when BCl 3 is used in place of BF 3· OEt 2 the ...