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2.3.4.5 α-Keto and β-Keto Acid Derivatives

DOI: 10.1055/sos-SD-202-00041

De Wildeman, S.; Sereinig, N.Science of Synthesis: Stereoselective Synthesis, (20112177.

α-Keto and β-keto acid derivatives are frequently used as substrates and have been intensely studied with bakerʼs yeast (Table 13 and Table 14).

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M8 M8 Meeeeee,e Meeeeee Meeeee ee (%) Meeeee (%) Mee
Me Me M MMMM M 88 eeee [‌88‌]
Me Me M MMM888e M >88 e.e. [‌888‌,‌888‌]
Me Me M MMM-MM-MMM M 88 88 [‌888‌]
Me Me e.e. MMMMM M >88 e.e. [‌888‌]
Me Me M MMM-Mee M >88 eeeee [‌888‌]
Me Me M MMM-MM M 88 eeeee [‌888‌]
Me 8-MeM8M8 M MMM888e M >88 8888 [‌888‌]
Me MM8MM8Me Meeeeeeeeeeee eeeeeeeeee (eeeeeʼe eeeee) M >88 88 [‌888‌]
Me Me M MMM888e M 88 88 [‌888‌]
Me Me M MM-MMM M >88 88 [‌888‌]
Me Me M MMM-MM M >88 888e [‌888‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me eMe M MMMM M 88 88 (eeee) [‌88‌]
Me eMe M MMM-MM M >88 88 (eeeeeee) [‌88‌]
Me eMe e.e. MMMMM M >88 e.e. [‌888‌]
Me eMe M MMM-MM M >88 888e [‌888‌]
Me e-Me M MMMM M >88 88 (eeee) [‌88‌]
Me e-Me M MMMM 888 M >88 e.e. [‌88‌]
Me e-Me M MMM-MM M 88 88 (eeee) [‌88‌]
Me Me e.e. MMMMM M >88 e.e. [‌888‌]
Me Me e.e. MMMMM M >88 >88e [‌888‌]
Me (MM8)8Me e.e. MMMMM M >88 >88e [‌888‌]
Me Me M MMMM M >88 eeeee [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M MMM-MM M >88 eeeeeee [‌888‌]
Me (MM8)8Me M MMM888e M >88 e.e. [‌88‌]
Me (MM8)8Me M eeeeeeeeeee eeeeeeeeeeeeeee eeee Meeeeeeeeeeee eeeeee M 88.8 88.8e [‌888‌]
Me (MM8)8Me M MMM-MM M 88 88e [‌888‌]
Me Me M MMMM M >88 eeeeeee [‌88‌]
Me Me M MMM888e M 88 88 [‌888‌]
Me Me M MM-MMM M >88 88 [‌888‌]
Me Me e.e. MMMMM M >88 e.e. [‌888‌]
Me Me M MMM-MMee M 88 eeeee [‌888‌]
Me Me M MMM888e M 88 eeeeeee [‌888‌]
Me 8-MeM8M8 M MMM888e M >88 e.e. [‌888‌]
Me 8-MM8M8 M MMM888e M 88 eeeeeee [‌888‌]
Me 8-MM8M8 M MMMM M 88 eeeeeee [‌88‌]
Me 8-MM8M8 M MMM-MMee M 88 eeeeeee [‌888‌]
Me 8-MeM8M8 M MMM888e M 88 eeeee [‌888‌]
Me 8-MeM8M8 M MMMM M 88 eeeeeee [‌88‌]
Me 8-MeM8M8 M MMM-MMee M 88 eeeee [‌888‌]
Me 8-MeM8M8 M MMM888e M 88 eeeeeee [‌888‌]
Me 8-MeM8M8 M MMMM M 88 eeeeeee [‌88‌]
Me 8-MeM8M8 M MMM-MMee M 88 eeeee [‌888‌]
Me 8-Mee M MMM888e M 88 eeee [‌888‌]
Me 8-Mee M MMMM M 88 eeee [‌88‌]
Me 8-Mee M MMM-MMee M 88 eeeeeee [‌888‌]
Me 8,8-M8M8M8 M MMM888e M 88 eeeeeee [‌888‌]
Me 8,8-M8M8M8 M MMMM M 88 88 (eeeeeee) [‌88‌]
Me 8,8-M8M8M8 M MMM-MMee M 88 eeeeeee [‌888‌]
Me 8-MMM8M8 M MMMM M 88 eeeee [‌88‌]
Me 8-MMM8M8 M MMM-MMee M 88 eeeee [‌888‌]
Me 8,8-Me8M8M8 M MMMM M 88 eeeeeee [‌88‌]
Me 8,8-Me8M8M8 M MMM-MMee M 88 eeeee [‌888‌]
M (MM8)8Me M e-eeeeeee eeeeeeeeeeeee eeee Meeeeeeeeeeeee eeeeeeeee M >88.8 eeeee [‌888‌]
M (MM8)8Me e.e. e-MeeMM eeee Meeeeeeeeeeee eeeee M >88 eeeee [‌888‌]

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M8 M8 Meeeeee,e Meeeeee Meeeee ee (%) Meeeee (%) Mee
Me Me M MMM-MM M >88.8 88 [‌88‌]
Me Me M MMM-MM M >88 88 [‌888‌]
Me Me M MMM-MM M >88 88e [‌888‌]
Me Me M MMM-M M >88.8 e.e. [‌88‌]
Me Me eeeee eeeee Mee8e M >88 88 [‌888‌]
Me Me eeeee eeeee Mee8e M >88 88 [‌888‌]
Me Me M MMM888e M >88 88 [‌888‌]
Me Me M MM-MMM M >88 88 [‌888‌]
Me Me M Mee-MMM8 M >88 >88 [‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌]
Me Me M MMM-MM M >88 eeee [‌88‌]
Me Me M MMM-MM M >88 888e [‌888‌]
Me Me M MMM-MM M >88 88/(eeee) [‌888‌]
Me Me M MMM-MMee M 88 eeeeeee [‌888‌]
Me Me M MMM M >88 eeeee [‌888‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌,‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌,‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌,‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌]
Me Me M MMMM 888 M >88 eeeeeee [‌888‌]
Me Me e.e. Meeeeeeeeeeee eeeeeeeeee (eeeeeʼe eeeee) M 88 e.e. [‌88‌]
Me Me eeeee eeeee Mee8e M >88 88 [‌888‌]
Me Me eeeee eeeee Mee8e M >88 88 [‌888‌]
Me Me M Mee-MMM8 M >88 >88 [‌888‌]
Me Me M MMM-MM M >88 >88e [‌888‌]
Me e-Me M Mee M >88 88 [‌888‌,‌888‌]
Me MM8e-Me M Mee-MMM8 M >88 >88 [‌888‌]
Me Me eeeee eeeee MMM-MM M >88 eeeeeee [‌88‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M Mee-MMM8 M >88 >88 [‌888‌]
Me Me eeeee eeeee Mee8e M 88 88 [‌888‌]
Me Me eeeee eeeee M >88 e.e. [‌88‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
Me Me M MMM888e M >88 e.e. [‌88‌]
eMe Me M MMM-MM M >88 eeeee [‌88‌]
eMe Me M MMMM 888 M >88 e.e. [‌888‌]
eMe Me M MMMM 888 M >88 e.e. [‌888‌]
eMe Me M MMMM 888 M >88 e.e. [‌888‌]
eMe Me M MMMM 888 M >88 e.e. [‌888‌]
eMe Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
e-Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMM-MM M >88 888e [‌888‌]
MM8Me Me eeeeeeeeeee eeeeee MMM-Mee M >88 88 [‌88‌]
MM8Me Me eeeee eeeee MMM-MM M >88 88.8 [‌888‌,‌888‌]
MM8Me Me MMM-MM M 888 e.e. [‌888‌]
MM8Me Me M MMM M >88 eeeeeee [‌888‌]
MM8Me Me M MMM-MM M >88 888e [‌888‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM-MM-MMM M 88 88 [‌888‌]
MM8Me Me M MMM-MM M >88 888e [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMMM 888 M >88 e.e. [‌888‌]
MM8Me Me M MMM-MMee M 88 88.8 [‌888‌]
MM8Me Me M MMM-MM M >88 88 (eeeee) [‌88‌,‌888‌]
MM8Me Me M MMM888e M 88 88 [‌888‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M MMM888e M >88 e.e. [‌88‌]
MM8Me Me M eeee-eeee MMM-MM M >88 888e [‌888‌]
MM8Me eMe M MMM-MM-M M >88 88e [‌888‌,‌888‌]
MM8Me Me M MMM-MM M >88 88 (eeeeeee) [‌888‌]
MM8Me eMe M MMM M 88.8 eeeee [‌888‌]
MM8M Me M MMM-MM M >88 88 (eeee) [‌888‌]
MM8MM Me M MMM-MM M >88 88 (eeeeeee) [‌888‌]
MM8 Me M MMM-MM M >88 eeee [‌88‌]
MM8 Me M MMM-MM M >88 88e [‌888‌]
MM8 Me M MMM-M-MM8 M >88 88e [‌888‌]
MM8 Me M MMMM 888 M >88 eeee [‌888‌]
MM8 Me M MMMM 888 M >88 eeee [‌888‌]
MM8 Me M MMM-M-MM8 M >88 88e [‌888‌]
eMe Me M MMM888e M >88 e.e. [‌88‌]
eMe Me M MMM888e M >88 e.e. [‌88‌]
eMe Me M MMM888e M >88 e.e. [‌88‌]
MM8MM=MM8 Me M MMM888e M 88 88 [‌888‌]
MM8MM=MM8 Me M MM-MMM M >88 88 [‌888‌]
(MM8)8Me Me M MMM888e M 88 88 [‌888‌]
(MM8)8Me Me M MM-MMM M >88 88 [‌888‌]
(MM8)8Me Me M MMM888e M >88 88 [‌888‌]
(MM8)8Me Me M MM-MMM M >88 8 [‌888‌]
Me Me M eeeeeeeeeee eeeeeeeeeeeeeee eeee Meeeeeeeeeeee eeeeee M 88.8 88.8 [‌888‌]
Me Me M MMM-MMee M 88 eeee [‌888‌]
Me Me M MMMM 888 M >88 e.e. [‌888‌]

e Meeeee M: eeeeeeee eeeeeeeeeeee eeee eMeMM; Meeeee M: eeeeeeee eeeeeeeeeeee eeee MMM; Meeeee M: eeeeeeee eeeeeeeeeeee eeee MMM; Meeeee M: eeeee eeeeee; Meeeee M: MMM eeeeeeeeeee eeee MMM; Meeeee M: eeeeeeee eeeeeeeeeeee eeee eeeeeee-8-eeeeeeeee eeeeeeeeeeeee; Meeeee M: MMM eeeeeeeeeee eeee MMM.

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