Science of Synthesis

Watson, I. D. G.; Toste, F. D., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 285.

The ene reaction tolerates a wide number of variants in terms of the enophile (see ‌Scheme 1‌). When a carbonyl group is used as the enophile, the reaction is often called the carbonyl-ene reaction.[‌92‌] A large number of intermolecular diastereo- and enantioselective variants of the carbonyl-ene reaction have been developed; however, there have been relatively few asymmetric intramolecular versions of this reaction disclosed (‌Scheme 41‌).[‌93‌]

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeeee-Mee Meeeeeeeeee Meeeeeee

Meeee eeeeeeeeee ee eee eeeeeeee eeeeeeee eeeee eeeeeeeeeeeeee eeeeee Meeee eeeee. Mee eeeeeee, e eeee–(M)-8,8′-ee-8-eeeeeeee [(M)-MMMMM] eeeeeeee (8 eeeee) eeeeeeee 8-eeeeeeeeeeeeeeeee (‌88‌, M8 = Me) eeee 88% eeeeeeeeeeee eeeeee, eeeeeee ‌88‌ (M8 = M) eeeeeee e eeeeeee eeeeeee (‌Meeeee 88‌).[‌88‌] M eeeeeeee eeeeeeee eeee e eeeeeeee-eeeeeee eeee ee eee eeeeee (8.8 eeeee) eeeeeeeeeeeeeee eeee-8,8-eeeeeee eeee eeeeeeeeee ‌888‌ ee eeeeeee eeee 88% eeeeeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌] Me e eeeeeee eeeee, eee eeeeee eeeeeeee Meeee eeee eeeeeeeee eeee eee eeeeeeeeeeeeeeeeeeee (88–88% ee) eee eee eeeeeeee-eee eeeeeeeeeee ee eee eee eeeeeeeeeeee ee eee eeeeeeeee ee eeeeeeeee, e eeeeeeeeeeeee eeeeeee eeeeeee.[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeeeeeeeeeeee Meeeeeee-Mee Meeeeeeeeee Meeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

Meeeee eee ee-eeeeeee eeee eeeeeeeee e eeeeee eeeeeeee eeeeeeeeeee–(M)-8,8′-ee-8-eeeeeeee eeeeee eee eee eeeeeeeeeee ee α-eeeeee eeeeeeeee.[‌88‌,‌88‌] Mee eeeeeeee eeeeeeeeeeeeee eeeeeeee eee eeeee-eeeeeeeeeee eee-eeeeeeee eeee ‌888M‌ eeee eeeeeeee eeeeeeeeeeeeeeeeee eee eee eee eeeeeeeeee eeee eeee eeee eeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeee Meeeeeee–(M)-8,8′-Me-8-eeeeeeee Meeeeeeee Meeeeeee-Mee Meeeeeeeeee Me Meee Mee-Meeeeeee Meeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

Meee eee eeeeee ee eeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeee ee eeeeeeeeeee eeeeeeee eee e eeeee-eeeeeeee-eeee eeeeeee ee eeeeee eeee eeee eeeeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeee Meeeeeee–(M)-8,8′-Me-8-eeeeeeee Meeeeeeee Meeeeeee-Mee Meeeeeeeeee Me Meee Meeee-Meeeeeee Meeee[‌88‌]

‌Meeeeeeeeee 88‌

Meee eee ee-eeeeeee eeee eeeeeeeee e Meeee eeee eeeeeeeee eeeeeeeeeee ee α-eee eeeeee ee eeeeee eeeeeeee. Me eee eeeeeee ee e eeeeeeee, eeeee eeeeeeeee eeeeeee ee eeee eeeeeeeeeee eeee eeeeeee eeee. Meeee eeeeeeeee eeeeeeeee eeeeeeeeeeee ee Meeee eeee eee eeeeee eee(8,8-eeeeeeeeeeeeee) eeeeeee, ee eee eeeeeeeeee eeee eee eeeeeee ee eeeeee(MM) eeee eeeeee (M,M)-‌888‌ [(M,M)-Me-eee] ee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeeee ee e eeeeee ee α-eee eeeeee ‌888‌ (‌Meeeee 88‌).[‌88‌] Mee eeeeeeee ee eeeeeeeee eee ‌888M‌, eeeee eee eeeeeee eee eeeee eeeee eeee e eee eeeeeeeeeee. Mee α-eee eeeee ‌888‌ (e = 8; M8 = M8 = Me), eeeeeeee eeee (+)-(M)-eeeeeeeeeee eeee, eeeeeeeee eee eeeeeeeeeeeee eeeeeeee eeeeeee ‌888‌ eeee eeeeee eeeeeeeee- eee eeeeeeeeeeeeee (ee 8.8:8, 88% ee) ee eee eeeeeee ee e eeeeee eeeeee; eeeeeee, eeee eee eeeeee (M,M)-‌888‌ ee eeeeeeee, ee eeeeeeeeeeeee ee eeee eee eeeeeeeee- eee eeeeeeeeeeeeeeeeee ee eeeeeeee (‌Meeeee 88‌). Mee eeee eeeeeee eeee ee eeeeeeee eee eeeeeeeee ‌888‌ (e = 8; M8 = Me; M8 = Me).

‌Meeeee 88‌ Meeeeeeeee Meeeee(MM)-Meeeeeeee Meeeeeeeeee ee α-Mee Meeeee[‌88‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-8-eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌88‌]

Meeeee eeeeee (M,M)-‌888‌ (88.8 ee, 8.88 eeee) eee Me(MMe)8 (88.8 ee, 8.88 eeee) eeee eeeee ee eee MM8Me8 (8 eM) eee 88 eee ee ee. Meee, α-eee eeeee ‌888‌ (8.88 eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee. Meee eee eeeeeeee eee eeeeeeee ee eeeee ee MMM, eee eeeeeee eee eeeeeeee eeeeeee e eeee eee ee eeeeee eee eee eeee eeeeeeeeeeee ee eeee ee eeeeeeeeeeee eeee eeeeeeee.

References