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36.9.1.1.2 Variation 2: Additions to Magnesium Enolates

DOI: 10.1055/sos-SD-036-00675

Mahrwald, R.; Schetter, B.Science of Synthesis, (200836855.

There are only a few examples of the deployment of magnesium enolates in aldol additions, although very early on successful applications in enantioselective aldolizations were reported in which deprotonation of the chiral sulfinyl acetate 41 with tert-butylmagnesium bromide and subsequent aldol additions yielded the aldol adducts 42 with moderate to high enantioselectivities (Scheme 13).[‌56‌‌58‌]

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Meeeeeeeeee 88

M8 M8 ee (%) ee 88 Meeee (%) ee 88 Mee
M (MM8)8Me 88 88 [‌88‌]
M MMMe 88 88 [‌88‌]
M MM(MM8)8Me 88 88 [‌88‌]
M Me 88 88 [‌88‌]
Me (MM8)8Me 88 88 [‌88‌]
Me MMMe 88 88 [‌88‌]
Me MM(MM8)8Me 88 88 [‌88‌]
Me MM8Me 8 88 [‌88‌]
Me MM8MM8MMe 88 88 [‌88‌]
Me Me 88 88 [‌88‌]
Me MM8 88 88 [‌88‌]

Meeee, e eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeeeee (88) eee eeeeeeee eee ee eeeeeeeee eeeeee ee eeee eeeeeee, eeee eeeeeee eeee eeee-eeeee eeeeee eeeeee, eeeeee eeee-eeeeeeeeeeee. Me eeeeeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeeee ee eeee eeeeeeee eee eeee eeeeeeeeeeee ee eeeeee eeeeee ee eeeee ee M-eee eeeeeeeee eeeeeeee ee ee eeeeeee eee.[‌88‌] Meee eeee ee eeeeeee eee ee eeeeeee ee eeee eeeee eeeee eeeeeeee 88 ee eeee ee eee eeee-eeeee eeeeeeee 88 (Meeeee 88); eeeeeee, eee eeeeeeeeeee ee eeeeeeeee eeeeee, ee eeee ee Meeeeeee eeeeeeee, ee eeeeee eeeee eeeeeeeee eeeeee eee eeeeeeeee ee eeeeeeeee, ee eeee eeeeeeeeeeee ee eeeeeeeeeee eeee eeeeeeeeee eeeeeeeee eee eeeeeeee.[‌88‌]

Meeeee 88 Meeee Meeeeeeee Meeeeeee ee Meeeeeeee Meeeeeeeeeeeeeeeeeeeee[‌88‌]

Mee eeee eeeeeeeee eeeeeeeeeeee ee eeeeeeeee ee eeeee eeeeeeeee eeeeeee eeeeeeeee eeeee; eeee eee ee eeee (8) ee eeeeeeeeeee eeee eeeee eeeee, (8) ee eeeeeeeeeeeeeee eeeeee eeee eee ee eeeeeeeee eeeeeee eeeeeeee, ee (8) ee Meeee eeeee ee Meeeeeeee eeeeeeeee. Me Meeeeee 88.8.8.8.8 (Meeeee 8) eee eee ee eeeeeeeee eeeeeee ee eeeeee ee eeeee eeeeeeeee ee eeeeeee eeeeeeee ee (8M)-8-eeeeeee-8,8,8-eeeeeeeeeeeeee eeeeeee (MMMMM, 88) eeeeeeeee ee Meeee'e eeeeeeeeeee ee eeeeeeeee. Meeeeeeeeeeeeee ee eeeeeeeee ee ee eeeeeeeeeee eee eee eeeeeeeeee eeee eeeeeeeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeee.[‌88‌] M eeeeeeeeee eeeee ee eee eeeeeeeeeee ee eeeeeeeee eeeee ee eeeee eeeeeeeee eee eeee eeeeeee eee (Meeeee 88).[‌88‌] Meeee eeeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeee eeeeeeeeeeeee eeeeee eee eeee-eeeeeeeeee eeeee eeeeeee 88M eeee eeeee eeeeeee 88M. Meee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeee eeeee ee eeeeeee eeeeeeeee eeeee eeeeeee eeeeeeeeeeeeeeee eeeee ee eeee ee eeeeeeee eee eeeeeee 88, eee eeee eee eeeee ee eeeeeeeeeeeeeee ee eeee eeeeee.

Meeeee 88 Mee Meeeee ee Meeeeeeee Meeee ee eee Meeeeeeeeeeeee Meeeeee ee Meeeeeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (e) Meeee (eeee/eee) Meeeee (%) Mee
MMMe MeMe8e
Me Me Me 88 88:88 88:8 88 [‌88‌]
Me Me Me 88 88:88 88:88e 88 [‌88‌]
(MM8)8Me Me Me 88 e 88:88 88 [‌88‌]
Me Me Me 8 88:88 88:88 88 [‌88‌]
Me Me Me 88 88:88 88:88 88 [‌88‌]
eMe Me Me 8 88:88 88:8 88 [‌88‌]
eMe Me Me 8 88:88 88:8 88 [‌88‌]
Me Me eMe 8.8 88:88 88:88 88 [‌88‌]
Me Me eMe 88 88:88 88:8e 88 [‌88‌]
(MM8)8Me Me eMe 88 88:88 88:88 88 [‌88‌]
Me Me e-Me 8 <8:88 88:8 88 [‌88‌]
(MM8)8Me Me e-Me 88 <8:88 88:88 88 [‌88‌]
Me MMe Me 8 88:88 88:8 88 [‌88‌]

e Mee eeeeeeee eeee eeeee MeMe8MMe8.

e Meeee eeeeeee eeeeee eeeeeeee eeee eee eeeeeee eeeeeee eeeeeeeee eeee MMM.

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Meeeeeeeeee 88

M8 M8 M8 Meeee (eeee/eee) Meeee (%) Mee
Me Me Me 88:8 88 [‌88‌]
8-MM8M8 Me Me 88:8 88 [‌88‌]
8-MeM8M8 Me Me 88:88 88 [‌88‌]
8-Mee Me Me 88:8 88 [‌88‌]
MM=MMMe Me Me 88:88 88 [‌88‌]
MM=MMMe Me Me 88:88 88 [‌88‌]
e-Me Me Me 888:8 88 [‌88‌]
Me (MM8)8 88:88 88 [‌88‌]
8-MeM8M8 (MM8)8 88:88 88 [‌88‌]
Me Me Me 88:88 88 [‌88‌]

Meeeeeeeeeeeee eeee eee eeeeeeeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeeeeeeee eeeee eeeeeee eeeeeeeee eeeee eeeeeeeee eeee eeee eeeeeee eee; eeee eeee eeee eeee-eeeeeeeee eeeee eeeeeeeee ee eeeeee M-eeeeeeeeeeeeeeeeee eeee eee-eeeeeeeeee eeeeeeeee eee eeeeeeeee ee 88eee% ee eee eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeee.[‌88‌] Me eeeeeeeee ee eeee eeeee eeeeeeeeeee eeee e eeeeee M-eeeeeeeeeeeeeeeeeeeeee, eeee ee 88, eee eee-eeeeeeeeee eeeeeeeee (Meeeee 88).[‌88‌] M eeeeeeeeee ee eeeee eee eeeeeee eeeee eeee eee eeeeeeeeee eeee-eeeeeeeeee eeeeee 88, eeeeeeee eeee eeeeeeeeeeee ee eee eeeeeeee eeeeeee ee eee M-eeeeeeeeeeeeeeeeeeeeee eeeeee, ee eeeeeeeeeeeee ee eee eeeeee 88, eeeeeee eeee e eeeeeeee eeee eeeeeee eee eeeeeeeeeeeee eeeeee M-eeeeeeeeeeeeeeeee. Meeee eeeeeeeee eeeeeeeeeeeeee eeeeeee eee ee eeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeee eeeeeeeeee eeeeee 88 eee 88 (Meeeee 88); eeeeeee eeeeeeeeeee eeee eee ee eeee eeee eee eeeeeee eeeeeeee eeee eee eeeee eeeeeeeee eeee ee eeee eeee.

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Meeeeeeeeee 88

M8 Meeee (eeee/eee) Meeee (%) Mee
Me 88:8 88 [‌88‌]
8-Mee 88:8 88 [‌88‌]
8-MeMM8M8 88:8 88 [‌88‌]
MM=MMMe 88:8 88 [‌88‌]
MMe=MMMe 88:8 88 [‌88‌]
8-eeeeeeee 8:8 88 [‌88‌]
MMe=MM8 8:8 88 [‌88‌]

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Meeeee 88 Meeeeeeeee ee Meeeeeeee Meeeee ee eee Meeee Meeeeeeee ee Meeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-8-eeeeee-8-eeeeeeeeeeee-8-eee (88, M8=eMe); Meeeeee Meeeeeeee:[‌88‌]

Me[M(MMM)8]8 (88, 8eeee) eee eeeeeeeee ee eeeeee (88eM) eee eee eeeeeee eee eeeeee ee 88°M. MeMMM (8eeee) eee eeeee, eeeeeeee ee 8-eeeeeeeeeee-8-eee. Mee eeeeeee eee eeeeeee ee 88°M eee 88eee, eee eeee eee eeeeeeee eee eeeeeeee eeee 8M MMe; eeeee: 88%.

(8M)-8-Meeeee-8-[(8M,8M)-8-eeeeeee-8-eeeeee-8-eeeeeeeeeeeeeee]eeeeeeeeeeee-8-eeeeee (88):[‌88‌]

MeMe8MMe8 (8.8eeee, 8.8 eeeee) eee eeeeee ee e 88-eM eeeee-eeeeeeee eeeee ee e eeeeeeee. Mee eeeee eee eeeeee eeee e eeeeee eee eee eeeeeee eeeeeeeeeeee eeee eee eeeeeeeeeeeeeeeeee 88 (8.8eeee, 8 eeeee), MeMMe (88.8eM), MeMMM (8.8eeee, 8.8 eeeee), Me8M (88.8eeee, 8.8 eeeee), eee eeeeeee eeeeeeeee MMMMe (8.8eeee, 8.8 eeeee). Mee eeeeee, eeeeee eeeeeee eee eeeeeee eee 8888e eeeee eeeeeeee eeeeeeeeee eee eeeeeeeee (MMM), eee eeee eeeeeeee eeeeeeee eeeeeee e eeee ee eeeeee eee (8.8ee × 8.8ee), eeeeeee eeee Me8M. Mee eeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeee eeeeeee eee eeeeeeee (8M MMM) ee eeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeee. Mee eeeeeeeeee eeeeeee eee eeeeeeeeeee ee MMM (888eM) eee eeeeeee eeee 8.8M MMe (88eM). Meeee eeeeeeee eee 8e, eee eeeeeee eee eeeeeee eeee Me8M (888eM) eee M8M (888eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeeeeeeeeeee eeee eee. ee MeMMM8 (888eM) eee eeeee (888eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee 8e, eeee eeeeeeee eeeeeee e eeeeee eeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee 8:8) eeeeeeee eee eeeee eeeeeeee (eee eeeee eeeeeeeeeeee) ee eee eeee ee e eeeeee eeee; eeeee: 88%.

References


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