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Please login or sign up for a free trial to access the full content. Method 6: Enzyme-Catalyzed Aldol Additions

DOI: 10.1055/sos-SD-036-00675

Mahrwald, R.; Schetter, B.Science of Synthesis, (200836928.

Enzymes, in particular aldolases, not only supplement classical methodologies, but they are useful tools in aldol additions where traditional procedures fail, such as in the syntheses of amino acids[‌472‌,‌473‌] and carbohydrates.[‌474‌‌479‌] Indeed, more and more enzymes are being employed in CC bond formation processes, especially in natural product synthesis,[‌5‌] and often a combination of enzymatic and classical routes are utilized to ensure that the final product is generated with the correct stereochemistry in place.[‌480‌]

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Meeeee 888 Meeeeeee Meeeeeeee Meee ee Meeee M Meeeeeeee[‌888‌]

Me eee eeeee eeee, eeeee MM eeeeeeeee eeeeeee e eeee eee ee eeeeeeee eee eeeeeee eeeeeeeee, eeeee ee eee eeee eeee e eeeeeeee eeeeeee eeee ee eeeeeeeee eeeeeee eeeeeee ee eee eeeeeeeeee ee eee eeeeeeee eeeeeeee. Meee eeeee eeeeee eeee eeeee eeeee, eee eeee-eeeee eeeeeee eeeeeeeee eeee eee eeeeeeee eeeeeeee ee eeeeeeeee ee Meeeee 888.[‌888‌]

Meeeee 888 Meeeeeee Meeeeeeee Meee ee Meeee MM Meeeeeeee[‌888‌]

Meeeeee ee eee eeeeeee eeeeeeee ee eeeeeeeeeee ee eeeeeeeee ee eeeeeee eeeeeeeee, e eeeee eeeeee ee eeeeeeeee eeeeeeeee eee eee eeeeeeeee eee eeeeeeeeeeee ee eeee eeee eeee eeee eeeeeeeeeeeeeee eeeeeeee.[‌888‌] Mee eeee eeeeee eeee e eeeeeeee eeeeee ee eeeeeeeeeeeeeee eeee ee eeeeeeeee eeee. M eeee eeeeeeeee eeeeee ee eeeeeeeee eeeeeee eeeeeeee eeeeeeeee eeee, eee eeeeeee, M-eeeeeeeeeeeeeeee eeee eeeeeeee (MeeM) eeeeeeeee eee eeeeeeeeee eeeeeeee ee eeeeeee eeee ee M-eeeeee-M-eeeeeeeeeee 888 ee eeee eee eeeee eeeeee 888, eee eeeeee ee eeeeeeeeee eeee (888) (Meeeee 888).[‌888‌]

Meeeee 888 M-Meeeeeeeeeeeeeee Meee Meeeeeee Meeeeeeee Meeee Meeeeeee ee Meeeeeee ee M-Meeeee-M-eeeeeeeeeee[‌888‌]

Meee eeeeeeeee eee ee eeeeeee eee eeee ee e eeeee-eee eeeee ee eeeeeeee eeeeeeee eeee ee e eeeeeeeee ee eeeeeeeee (888), e eeee eeee eeeeeee eeeeeeeee. Meee eeeeeeeee, eeeee eeeeee eeee eee eeeeeeeeeeeee ee eee 8-(eeeeeeeeeee)-8-eeeeeeeeeeeee 888, eeeeeeeeee eee eeeee ee eeeeeeeee ee eeeeeeeeee eeeeeeeee; ee ee eeeeeeeeee ee Meeeee 888.[‌888‌]

Meeeee 888 Meeeeeeeee Meeeeeeeeee ee M-Meeeeeeeeeeeeeee Meee Meeeeeee ee eee Meeeeeeee ee Meeeeeeee[‌888‌]

M-Meeeeeeeeeeeeeee eeee eeeee (MMM) eeeeeeee eeee eeeeee eeeeeeeeeee eeeeee MM eeee eeeeeeeee, eee ee eeee, eee eeeeeee ee e eeeeeeee ee eeeeeeeee ee eeeeeee. Meeeeee, ee ee eeeeeee eeee eeeeeeeeeeee eee eeeeeeeeee ee eeeeeeee eeeeeeeee ee eeeeee eeeeee,[‌888‌‌888‌] eee eeeeeeeeeeeeee eeeeee ee M-eeeeeeeeeeeeeeee eeee eeeee eeeeeeeee MM eeee eeeeeeeee eee ee eeeeeeeeee eee eeee eeeeeeeeee eeeeeee.[‌888‌] Meeeeee eeeeeeeee eee eeee ee eeee ee eee eeeeeeeee ee eeeeeeeee; eee eeeeeeee, eee eeeeeeeeee eeee eeeeeeee 888 ee eeeeeeeee eeeeeee ee eeeeeeeee eeeee eeeeeeee eeeeeee 8-eeeee-8-(eeeeeeeeeeeee)-M-eeeeeeeeeee (888) eee eeeeeeee. Me eee eeee ee eeeeeeeee ee eeeeeee eeeee, eee eeeeeeee 888, eeee eee eeeeeeeeee eeeeeeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 MeeM-Meeeeeee Meeeeeeeeeee ee eee Meeeeeeee ee ee Meeeeeeeee Meeeeeee[‌888‌]

8-Mee-8-eeeee-8-eeeeeee-M-eeeeeeeee eeeeeeee (MMMMee) ee e eeeee M eeeeeeee eeee eee e eeeeee eeeee eeeeeeeee eeeeeeeee eee eeeee eee eeeee eeeee eeeeeeeee. Mee eeeeeee, ee eeeeeeee eeeeeeee eeeeeeeee eeee eee eeeee eeeeeeeee 888, 888, eee 888 eee eee eeeeeeeeee, eeeeeee eee eeeeeeeeeeeee eeeee eeeeeee eeee eeee eee M eeeeeeeeeeeee ee M8. Meeee eeeeeeeee eeee eeeeeee eeeeeeeee eeee eeee eeeeeeeeeeeeeeeeeeeeee, eee eee eeeeee eee eee (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee ee 8-Mee-8-eeeee-8-eeeeeee-M-eeeeeeeee Meeeeeee[‌888‌,‌888‌]

Meeeeeee eeeee eeeeeeeee eeee M-eeeeeeeeeeeeeeee eeee eeeeeeee ee 8-eee-8-eeeee-8-eeeeeee-M-eeeeeeeee eeeeeeee eeeeee eeee eee eee eeeeeeeeeee eeeeee, eee eeeeeeee eeeee eeeeeee eeee ee-eeeeee eeeeeee eeeee eeeeeeeee. Me eeeeeeee, eeeeeeeeeeeeeeee eeeeeeeee eeeeeeeee eeeeeeee eeeee eeeeeeeee ee eeee eeeeeee eeeeeeeeeeeeeeee eeeeeeeeeeeee (888, MMMM) eee eeeeeeeeeeeeeee 888 ee eeeee eee eee eeeeeeeeeee eeeeeee eee eeeeee ee eee eeeeeeee eeee eeeeeeeee eeee eeeeeeeeeee. Meeeeeee eeee eeeeeeeee eee eeeeee eeeeeeeee, ee ee eeeeeeeee ee eeeeeeeee eeee eeee eeeee ee eeeeeeeee eeee eeeeeeee eeeeee­eeeeeeeeeeeee eee eeee eeeee eeeeeeeee eeeeeeeeee eeeee.[‌888‌‌888‌] Meeee eeeeeeeee eee: M-eeeeeeee 8,8-eeeeeeeeeeee eeeeeeee (MeeM), M-eeeeeeee 8,8-eeeeeeeeeeee eeeeeeee (MeeM), M-eeeeeeeeee 8,8-eeeeeeeeeeee eeeeeeee (MeeM), eee M-eeeeeeee 8,8-eeeeeeeeeeee eeeeeeee (MeeM). Meee eeeeeee eeeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeee ee eeee ee eee eeeeeee eeeeeeeeeeeeeeee eeeeeeeee-eeeeeeeee eeeeeeeee eee eeeeeeee ee Meeeee 888.[‌888‌‌888‌]

Meeeee 888 Meeee Meeeeeeee Meeeeeeee ee eee Meee Meeeeeeeeeeeeeeeeee Meeeeeeee-Meeeeeeee Meeeeeeee[‌888‌‌888‌]

Meeee eeeeeeeeeeee eeeeeeeee eee eeeee eeeeeeeee eeee eeee eeeeeeee (MeeM,[‌888‌] MeeM,[‌888‌] MeeM,[‌888‌] eee MeeM[‌888‌]); eee eeeeeee, MeeM eee MeeM eee eeee eeeeeeee eeeeeeeeeeeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeee eee eeeeee eeeeee e eee-888M ee ee eeee-888M eeeee eeeeee ee eee eeeeeeeee eeeeeee (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee ee M-Meeeeeeeee 8-Meeeeeeee eee M-Meeeeeee 8-Meeeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 888

M8 MeeM MeeM Mee
Meeeeeee Meeee Meeeee (eee/eeee) Meeee (%) Meeeeeee Meeee Meeeee (eee/eeee) Meeee (%)
M-MM(MM)Me 888 >88:8 88 888 <8:88 88 [‌888‌]
MM8MM 88 >88:8 88 88 <8:88 88 [‌888‌]
M-MM(MM)MM8MM 88 >88:8 88 88 <8:88 88 [‌888‌]
MM8MM8MM 88 >88:8 88 88 <8:88 88 [‌888‌]
MM(MM)MM8MMe e.e. >88:8 88 e.e. <8:88 88 [‌888‌]
MM(MM)MM8M8 e.e. >88:8 88 e.e. <8:88 88 [‌888‌]
MM(MM)MM8M e.e. >88:8 88 e.e. <8:88 88 [‌888‌]
M 88 e.e. 88 88 e.e. 88 [‌888‌]
Me 88 88:88 88 88 8:88 88 [‌888‌]
eMe 88 88:8 88 88 88:88 88 [‌888‌]

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Meee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeee eeeeeeee eeeee ee eeeeeeeeee eeeeeeeee, eeeeeeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeee.[‌888‌] Meeeeeee ee eeeeeeeeeeeeee eeeeeeeee eee eeee ee eee eeeeeeeee ee M-eeeeeee,[‌888‌] M-eeeeeee (MeeM),[‌888‌,‌888‌] M-eeeeee eee eeeeeeeeeee (MeeM),[‌888‌,‌888‌] eeeeeeeeee,[‌888‌,‌888‌] eeeeeeeeeeeeeee eeeeeeeee ee 8-eeeeeeeeeeeeee,[‌888‌‌888‌] eeeeeeeee eee eeeeeeeeeeee (MeeM),[‌888‌] eeeeeeeeee (MeeM),[‌888‌] eeeeeeeeeee (MeeM),[‌888‌] eeeeeeeeee (MeeM),[‌888‌] eeeeeeeeee,[‌888‌] eeeeeeeeeeeeeeee eeeeeeeeeeee (MeeM),[‌888‌,‌888‌,‌888‌] eeeeeeee (MeeM),[‌888‌,‌888‌] eeeeeeeeeeeeeeee eeeeeeeeeee (MeeM[‌888‌] eee MeeM),[‌888‌‌888‌] eeeeeeee,[‌888‌] eeeeeeeeeeee,[‌888‌] eee eeeeeeeeee.[‌888‌] Meee, eee eeeeeeeee ee e eeeeeeeeee ee M-eeeeeee[‌888‌] eeeeee eeeeeeee eee eeeeeeeeee ee ee eeeeeee eeeeeeee ee M-eeeeeeeeeeeeee eee eeeeeeeeeeeeeeee eeeeeeeeeeeee eeee eee eeeeeeee MeeM ee eM 8.8. Mee eeeeeee ee eeeeeeee ee eeeeeee eeeeeee ee eee-eeeeeeee eeeeee eee, eeeee eee eeeeeeee eee eeeeeeeeeeeeee eeee eeeeeeeeeeeeeee, eeeeeee M-eeeeeeeeeeeee 8-eeeeeeeee eee(eeeeeeeeeeeeeeeeee) eeee ee 88% eeeee. Meeeeee eeeeeeeee eeeeeeeeeee ee eeee eeeeeeeeeee eeeeeeee eee eeeeee eeeeeeeeee/eeeeeeeeeeee ee eee eeeeeeeeeeeeeee 888. Meee, eeeee eeeeeeeee eeeeeeee, eee eeeeeeeeee 888 ee eeeeee eee eee eeeeee eeeeeeeeee 888 eeee eeeeeeeee eee eeeeeeeeeee eeeee eeeeeeeee eeee eeeeeeeeeeeeeeee eeeeeeeeeeeee (888) ee eeee eee eeeeeeeeeeee eeeeeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeeeeee Meeee Meeeeeeee ee Meeeee Meeeeeeee Meeee Meeeeeeee[‌888‌]

Meee eeeeeeeeeeeeee eee ee eeeeeeee ee eeeee eeeeeeeeee ee eeeeeeeeeee ee Meeeee 888 eeeee M-eeeeeeee 8,8-eeeeeeeeeeee eeeeeeee (MeeM) eeeeeeee eeeeeee eeeeeee eeeee eee eeeeeeeeeeeeeeee eeeeeeeeeeeee eeee eeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeee eeeeeee. Mee eeeeeeeee ee eeeeeeee ee eeeeeeee eeeeeeeeee eeeeeee ee eee eeeeeeeeeeee eeeeeee ee eee eeeeeee eeeeee ee eee eeeeeeee eeeee.[‌888‌]

Meeeee 888 Meeee ee eee Meeeeeeeeee Meeeeeeeeeeee ee Meeeee-Meeeeeeee Meeee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee[‌888‌]

Me eeeeeeee ee eeeeeeeeeeeee eeeeeee eeee eeeee eeeeeeeee eeeeeeeee ee 8-eeeee-M-eeeeee 8-eeeeeeeee eeeeeeeee (MeeM). Mee eeeeeee, e eeeeeeee eeeeeeeee ee Meeee 8 eeeeeeeee eeeeeeee ee eeeee eeeeeeee eeeeeee eeeeeeeeeeee eee M-eeeeeeeeeeeeee eeeeeeeee ee eeee eee eeeeeeeee eeeeeeeee eeeeee 888. Meeeeee eeeeeeeee eee eeeee eeee eeeee eeeeee eeee ee eee eeeee eeeeeeeee eee eeee; eeee, eeee 8-eeeeeeeeeeeeee ee eee eeeeeeeee, eee eeeeee eeeeeee ee eeeeeeeeeeeee eee eee eeeeeeee eeeeeeee, eee eeeeeeeeeeeee eeeeeee 888 eee 888 eee eeeeee. Me eeee eeee eee eeeeeeeeeeee β-eeeeee eeee ee eee eeeee eeeeee ee M-eeeeeeeeee (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeee-Meeeeeeee Meeeeeeee ee β-Meeeeee Meeeeeeee[‌888‌,‌888‌]

Me eeeeeeeee eeeee eeeeeeeee eeeeeee 8-eeeee-M-eeeeee 8-eeeeeeeee eeeeeeee eeeeeeeee e eeeeee ee eeeeeeeee α-eeeeeee eeeeeeeee 888 eee eeeee eee eee-eeeee eeeeeee 888 (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee ee Meeee-M-eeeeee 8-Meeeeeeee Meeeeeee Meeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 888

M8 Meeee (%) Mee
MM8MMM88 88 [‌888‌]
MM8MM 88 [‌888‌]
Me 88 [‌888‌]
MM8M 88 [‌888‌]
MM8Me 88 [‌888‌]
MM8Me 88 [‌888‌]
MM8MM 88 [‌888‌]

Me eeeeeeeeeee ee eeeee eeeeeeeeeeeeeee ee eeeee ee eee eeeee eeeeeeeee ee eeeeeeeeee M (888). Meee, eee eeeeeeeee eeeee-M-eeeeee 8-eeeeeeeee eeeeeeeee eee eeee ee eeeeeee eee eee- eee eeee-eeeeeeeeee eeeeeeeee 888 eee 888. Meeee eeeeeeeee eee eeee eeeeeeeee eeee eee eeeeeeee eeeeeeeee 888 eee 888 eeee eeeeeeeeee eeeeee eeeeeeee 8 ee 8, eeeeeeeeeeee, ee eee eeeeee eeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee Meeeeeeeee M Meeee MeeM-Meeeeeeee Meeeeeeee ee 8,8- eee 8,8-eeeee[‌888‌]

Mee eeeeeeeeee ee α-eeeee-β-eeeeeee eeeee eeee eeeeeeee eeeeeee eeee eeeeeeee eeeee eeeeeeeee eeeeeee eeeeeeeee eee α-eeeee eeeee. Meeee eeeeeee eee ee eeeeeeee ee eee eeeeeeeee ee eeeeeee eeeeee α-eeeee-β-eeeeeee eeee eeeeeeeeeee.[‌888‌‌888‌] Meeeeee, eeeeeeee eee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeeee ee eee, eeee eeeeee eeeeeeeeeeee eee eeeeeeee ee eeee eee eeeeeeeee ee eeeeeeeeeeeeeeee[‌888‌] eee eeeeeeeeeeee[‌888‌] eee ee eeeeeeee.