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Wang, S.-H.; Tu, Y.-Q.; Tang, M., Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (2015) 1, 307.
The most common way to terminate a domino cyclization initiated by a carbonyl or its derivatives is through the use of a nucleophile. Johnson and Kinnel first reported acetal-initiated cationic polyene cyclization.[86] Since their pioneering work, such reactions have been further developed for the efficient construction of polycycles.
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Meeee 8 Meeeee(MMM) Meeeeee Meeeeeee Meeee–Meeeeee Meeeeeeeeeee[88]
Meeee eeee Meeee–eeeeeee eeeeeeeeeee ee eeee eeeeeee 88 ee eee eee eeee, Mee eee ee-eeeeeee eeeeeeeee eee eeeee eeeeeeeee ee (±)-eeeeeeeeee eeee eeeeee eeeee (Meeeee 88).[88]
Meeeee 88 Meeee Meeeeeeee ee (±)-Meeeeeeeee Meee Meeeee Meeee[88]
Meeeeeeeeeeee, eeeeeeeeeeeeee Meeee–eeeeeee eeeeeeeeeeee ee eeee eeee eeeeeeeee eeeeeeeeee eeee eeeeeeeeeeeeee eeeeeeee. Meeeeee, eeeeeeeeeee eeeeeeeeeee ee eee eeeeee eeeeee eee eeeeeeee eee eeeeeee eeeeeeeee. Meeeeeee, eeeeeee eeeeee ee eeeeeee eee eeeeee eeee eeeeeeee, eee eeeeeee eeeeeeeee eeeeeee eeee eeeeeeee eeeeee eee eeeeeee eeeeeeeeeee; eeeeeee, eee eeeeeeeeeeeee eeeeeeeeeee eee eeee ee e eeeeeee eee eee eeeeeeeeeeeeeeeeeeee. Meeʼe eeeee eee eeeeeeeee eeeeeeeeee eeeeeee ee eeee eeee ee eeeeeeee (Meeee 8).[88–88] Me eeeeeeeee, eee eeeeee eeee eeeeeee eeeeeee eee eeeee eeeeeee eee eeeeeee eeeeeeeeee eeeeeee eee eee eeeeeeeeeeee eeeeeee. Meeee eee eeeeeee eeeeee, eeeeee eeeeeeee eeee eeeeee eeeeeee eeee eee eeeeeee eeee. Meeeeeee, eee eeeeeeeeee eeeeeee ee eeee eeeeeeee eeee eee eeee eeeeeeeee ee eeeee ee eeeeeeeeeee eeeeee eeeeeeeee eee eeeeeee ee eee eeeeeeeeeeeeeeee eeeee eeeeeeeee ee eeeeeeeee eeee (Meeeee 88).[88] Meeeeeeeeee, eee eeeeeeee eeeeeeeeeeeeee eeeeee ee eee eeeeeeee eeeee eeeeee eee eeeeeeeeʼe eeeeeeeeeee ee eeeee eeeeeeee.
Meeee 8 Meeeeeeeeeeeee Meeee–Meeeeee Meeeeeeeeeee[88]
Meeeee 88 Meeee Meeeeeeee ee Meeeeeeee Meee[88]
Meeeeee eeee ee eeeeeeee-eeeeeeeee eeeeee eeeeeeeeeee ee eee eeeeeeeeeeee ee eee-eeeeeeeeee eeeeeeeee. Me eeeeee ee eeeee eeeeeeee eee eeeeeeee eeee eeee ee eeeeeeeeeeee eeeeeee, eeee eeeeeeeeeeeeeee eee eeeeeeeee ee eeee ee e eeeeee eeeeee eee eee eeeeeeeee ee eeeeeeeeee eeeeeeeee eeeeeeeeee eeeee-eeee eeeeee. Mee eeeeeee eeeeeee ee eee eeeee eeeeeeeee ee eeeeeeeeeee-8 (Meeeee 88).[88,88] Me eeee eeeeeeeeeee eee eeeeeeeeeee eeee, eeeeeeeeeeeeeee eee eeeeeeeeee ee eee eeeee eeeeeeeee eee eeeeeeeee eeeeeeeeeee,[88–888] Meeeeeee eee ee-eeeeeee eeee eeeeeeeee eeee eeeeee eeeeeeeeeeeeeee, eee ee eeeee ee eee Meeee eeee eeeeeee eeeeee eeeeeeeeeee eeeeeee ee eee eeeeeeeeeeeeeeeeee MMMM-eeee eeeeee ee eeeeeeeeeee-8. Meeeee eeeee eeeeeeee ee eeeeeeee eee eeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeee-8, eeeeeee eeeeeeeeee eeee eeeeeeeee ee eeee eeeeee eeeeeeeeeee. Meee eeeeee eee Meeee eeeee eee eeeeeee eeee eeeeeeee, eeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee eeeeee eee eeee eeeeee (Meeee 8). Meee, ee eeeeee ee eeeee eeee eeeeeeee eee eeeeeeee eeeeeeeeeee eeeee ee eeeeeeeee ee eee eeeeeeeeeeeeee eeeee ee eee eeeeeeee.
Meeeee 88 Meeeeeeee ee Meeeeeeeeee-8[88,88]
Meeee 8 Meeeeeeeeeeeee Meeeeeeeeeeeeeeeeeeeeeeee Meeeeeee Meeeee Meeeeeeeeeee[88,888]
Meeeeee eeeeeee eeeeeee ee eee eeeeeeee ee eee eeeeeeeeeee eeee eeee eeeeee ee (+)-MM-888,888 ee eeeeeeee ee Meeee eee ee-eeeeeee (Meeeee 88).[888] Me e eeee eeeeeeeee eeeee eeeeeeeee ee eee eeeeee eeeeeeee, eeeeeeeee ee eeeeeeee eeeeeeeeeeee 88 eeee eeeeeeeee eeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee eeeee ee eee eeeeeee eeeeee eeeeeeee, eeeeeeeee eeeeeee 88 ee eeeeee eeeeeeeeeeee eeeee. Meeeee eeee eeeeeeee, eeeee eeee eee eeeeeeeeeeee ee eee eeee eeee eeeeee eee M88 eeeeeeeeee eeeeee eeeeee, e eeee eeeeeee eeeee ee eeee eeeeeeee eee eee eeeeeeeee eeeeeeeeeeee.
Meeeee 88 Meeee Meeeeeeee ee (+)-MM-888,888[888]
Meeeeeeeeeee Meeeeeeee
(8M*,8eM*,88eM*)-8-(Meeeeeeeeeee)-8-eeeeeee-88e-eeeeee-8,8,8e,8,8,88e-eeeeeeeee-8M-eeeee[e]-8-eeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
Me eeee-eeeee 88-eM eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee 8-Å eeeeeeeee eeeeee (888 ee) eee MeMe8 (8.88 eeee) eee eeeeee eeee e eeeeee eeeeee. Meee, (M)-8-(8-eeeeeeeeeeeee)-8-eeeeeeeee-8-ee-8-ee (8.88 eeee) eee 8-eeeeee-8,8-eeeeeeeeeeeeeee (8.88 eeee, 8.8 eeeee) eeee eeeeeeeee ee eee MM8Me8 (8 eM) eee eeeee eee eeeeeee. Mee eeee eee eeeeeee ee ee eee 88–88 e. Mee eeeeeeee eee eeeeeeee eeee eee. ee MeMMM8 (8 eM) eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 88%.
References
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