Intramolecular Simmons-Smith reaction and other synthetic alternatives to cyclopropanation of dienic diazo ketones. Parallel decomposition pathways of a sterically …

T Hudlicky, BC Ranu, SM Naqvi…

Index: Hudlicky, Tomas; Ranu, Brindaban C.; Naqvi, Saiyid M.; Srnak, Ana Journal of Organic Chemistry, 1985 , vol. 50, # l p. 123 - 127

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Abstract

5a. RI= R2= H 5b, Ft1= H: Rp= CH3 ““IC5c, R1 SR 2= C H3 la, R1= Rp= H lb. Ri= R2= CH3 a Reagents:(i) CH, CHMgBr/THF;(ii) RCH, C (OEt),/H+/A;(iii) KOH/H, O;(iv)(CH,), CHCOCl/Et, N, then LDA/THF (-78 “C--t 25 “C);(v) LDA, THFiMeI;(vi)(COCl),/benzene;(vii) CH, N,/Et 0. in eq la2 We assumed that the reversal of the order of the ring-closing sequence of this methodology applied to the diazoketone 1 depicted in eq 2 would eventually lead to the ...