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3.5.3 Carbonyl-Ene Reaction

DOI: 10.1055/sos-SD-203-00165

Watson, I. D. G.; Toste, F. D.Science of Synthesis: Stereoselective Synthesis, (20113285.

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]

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

Meeeeeeeeee 88

M8 ee (%) Meeee (%) Mee
Me 88 88 [‌88‌]
M 8 88 [‌88‌]

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

Meeeeeeeeee 88

M Meeee (888M/888M) ee (%) ee 888M ee (%) ee 888M Meeee (%) Mee
M 88:88 88 88 88 [‌88‌]
MM8 88:88 88 88 88 [‌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]

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Meeeeeeeeee 88

M8 ee (%) Meeee (%) Mee
M 88 88 [‌88‌]
Me 88 88 [‌88‌]

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

Meeeeeeeeee 88

e M8 M8 Meeeee Meeee (888M/888M) ee (%) ee 888M Meeee (%) Mee
8 Me M (M,M)-Me-eee [(M,M)-888] >88:8 88 88 [‌88‌]
8 Me M (M,M)-Me-eee [(M,M)-888] >88:8 88 88 [‌88‌]
8 Me Me 8.8:8 88 88 [‌88‌]
8 Me Me (M,M)-Me-eee [(M,M)-888] 88:8 88 88 [‌88‌]
8 Me Me (M,M)-Me-eee [(M,M)-888] 8.8:8 88 88 [‌88‌]
8 Me Me 8:8 88 88 [‌88‌]
8 Me Me (M,M)-Me-eee [(M,M)-888] 88:8 88 88 [‌88‌]
8 Me Me (M,M)-Me-eee [(M,M)-888] 8.8:8 88 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

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

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References


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