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Please login to access the full content or check if you have access via Variation 2: Conjugate Addition Reactions

DOI: 10.1055/sos-SD-003-00274

Heaney, H.; Christie, S.Science of Synthesis, (20043611.

Vinylcuprates are among the most effective reagents for conjugate addition reactions. In general, ethereal solvents, in particular tetrahydrofuran, are used. The reaction is even more efficient when a trapping agent is used (e.g., in the reaction to give 125), further highlighting the utility of 1,4-addition protocols. The three examples in Scheme 469 illustrate how different trapping agents will react through oxygen or carbon, and that functionalized cuprates can be employed.[‌1588‌,‌1589‌]

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Meeeee 888 Meeeeeeeeeeeeeee Meeeeeeee Meeeeeee ee Meeeeeeeeeeee ee Meeeee Meeeee[‌8888‌]

Mee eee ee eeeeeee eeeeeeeee ee eeeeeee eeeeee ee eeeeee eeeeeeeeeeeeee eeeeeeee eee ee eeee eeeeeeee MM eeeee ee eeee eeeeeeeeeee ee eeeeeeeee eeeeeeeee (e.e., ee eeee 888, Meeeee 888). Meee, eee eeeeeee eeeeee eeee eee eeeeeee 8,8-eeeeeeee ee eeee ee e eeeeeee eeeee eeeeeeee. Mee eeeeeeeeeeeeeee ee eee eeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeeeee.[‌8888‌,‌8888‌]

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Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-(eeeeeeeeeeeeeee)-8-eeeeeeeeeeeeee-8-eee (888); Meeeeee Meeeeeeee:[‌8888‌]

MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee (MMMM) ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.

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(8M,8M,8M)-8-[(8M)-8-Meeeeeeeee-8-eeee]-8-eeeeeeeeeee-8-eeeeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌8888‌]

MM8=MMMeMe (8 eeeee) eee eeeee ee MeMe (8 eeeee) ee Me8M eee eee eeeeeee eeee (M)-()-8-eeeeeeeeeeeeeeeeeee-8-eeeee. Mee eeee eee eeeeeee eee 8888eee ee 88 ee 88°M eee e eee. eeee ee MeMe8 (88 eeeee) ee Me8M eee eeeee, eeeeeeee ee e 8- ee 8-eeee eeeeee ee eeeeeeeeeeeeee [(8M)-eee-8-eeee]. Meeee eeeeeeee eee 88eee, eee eeeeeee eee eeeeeeee eeee ee eeeeee ee 88% MM8Me (eM8) eee eee eeeeeee eeeee eeeeeeeee. Mee eeeeeee eeeee eee eeee eeeeeeeee eeee Me8M (8×) eee eee eeeeeeee eeeeeee eeeeee eeeeee eeee 88% MM8Me (eM8), M8M, eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee ee eeee eee eeeeeeee β-eeeeeee eeeeeee (<88%); eeeeeeee eeeee: 88%. Meeeeeeeee ee MMMM (eeeeee eee) eeee eee eeee eeeeeee ee eeeeeeeee eeee (β-888, 88%; α-888, 88%).