Science of Synthesis

Lee, D.; Reddy Sabbasani, V., Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (2016) 2, 544.

In 1980, Villemin[‌1‌] and the Tsuji group[‌2‌] independently disclosed the first diene ring-closing metathesis using tungsten-based catalysts for the preparation of macrocycles from dialkenyl oxo esters and dialkenyl ketones. In 1993, Grubbs and coworkers reported a more efficient carbocyclization of 1,6-diene ‌3‌ with molybdenum-based carbene complex ‌1‌ as catalyst to generate cyclopentene ‌4‌ in high yield,[‌3‌] and subsequently with relatively air-stable ruthenium–alkylidene complex ‌2‌ (‌Scheme 3‌).[‌4‌] After this breakthrough, the development of more effective and user-friendly catalyst systems as well as their application to a variety of ring-closing metathesis reactions have been realized.

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‌Meeeeeeeeee 8‌

Me 8888, Meee eee eeeeeeeee eeeeeeee eee eeeee eeeeeee ee eeeee eeee-eeeeeee eeeeeeeeee ee eeeee e eeeeeeeeeeeeee eeeeee ee e eeeeeeee Meeeeee eeeeeee eeeeeee.[‌8‌,‌8‌] Mee eeeeee ee Meee eee Meee eeeeeeeeeeeee eeeeeeee eeeee eeee-eeeeeee eeeeeeeeee eeee eeeeeeee eeeeeeee ee Meeeeee eeeeeee eeeeeeeee,[‌8‌–‌88‌] eeeeeeee eeeee eeeeeeeee eeeeeee eeeeeeee eeee eee eeee eee eeeeee eee eeeeeeeeeee eeeeeeeee eeeeeeeee eee eeee eeeeeee eeeeeeeeee eeeee eeeeeeeee eee eeee eeeeeeee eeeeeee. M eeeeeeeeeee eeeeeeeeeee ee eeeeeeeee eeeee eeee-eeeeeee eeeeeeeeee eee eeeeeeee eeeee eeeeeeeee–eeeeeeeeee eeeeeee ‌8‌; eeee e eeeeeeeee eeeeee ee ‌8‌ (8 eee%), eeeee ‌8‌ eee eeeeeeeeeee eeeeeeeee eeee eeeee ‌8‌ (‌Meeeee 8‌).[‌8‌] Meeeeeeeeeee, Meeeee eee eeeeeeeee eeeeeeeee eee eeeeee eeeee eeee-eeeeeee eeeeeeeeee ee eeeeeeee ee eeeeeeeee eeeee eeeeeeee eeeeeeeeee eeeee eee eeee eeeeeeee.[‌88‌] Meeee ee eeeee eeeeeee eeeeeeeeeeeee, eeee eeeeeeeeeeeee eeeee eeeeeeeeee eeeeeeeeee eeee eeeeeee.

‌Meeeee 8‌ Meeee Meeeeeeee Meeeeeeee Meeeeee Meeee Meeee Meee-Meeeeee Meeeeeeeee[‌8‌]

Me 8888, eee Müeeeeee eeeee eeeeeeeeeeee ee eeeeeeeee eeee-eeeeeee eeeeee eeeeeeeeee (MMMM) ee eeeee ‌8‌ ee eeeeeeee eeeeeeeeee ‌88‌ eeeee eeeeeeee–eeeeeeeeee eeeeeee ‌8‌ (Meeeeee eeeeeeeeee),[‌88‌] eeeeeee eeeeeeee ee eeeeeeee eeeeeeeee eeeeeee ‌8‌[‌88‌] eeee eeee-eeeeeeeeeeeeee (‌Meeeee 8‌). Me 8888, eee eeee eeeee eeeeeeee eee eeee-eeeeeee eeeeee eeeeeeeeee eeee ee eeee eeeeeeeee eeeeeeeeee–eeeeeeeeee eeeeeee eeee eeeeeeeeee(MM) eeeeeeee.[‌88‌] Meeee eee eeeeeeee eeeeeee eeeeee e eeeeeee eeee ee eee eeeeeeeeee eeeeeeeeeee ee eeee-eeeeeee eeeeee eeeeeeeeee, eeeee eee eeee eeeeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeeee-eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeee eeeeeeee ee M/M-eeeeeeeee eeeeeeeeeeeee.

‌Meeeee 8‌ Meeee Meeeeeeee Meeeeeee–Meeeeeeeee Meeee Meee-Meeeeee Meeeee Meeeeeeeee[‌88‌,‌88‌]

References