Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

Table 1

Asymmetric reduction of 2-halo-1-(4-substituted phenyl)-ethanones 1a-j mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182^a.

Ketone	Microorganism	T (°C)	Alcohol	Yield (%)	[𝛼]^25D^b
1a	Geotrichum candidum	28	(S)-2a	96.4	+40.0
1b	“	28	(S)-2b	95.1	+38.7
1c	“	28	(S)-2c	96.0	+48.3
1d	“	28	(S)-2d	98.0	+19.8
1e	“	28	(S)-2e	97.6	+25.0
1f	“	28	(S)-2f	99.4	+35.0
1g	“	28	(S)-2g	95.0	+48.3
1h	“	28	(S)-2h	96.4	+48.3
1i	“	28	(S)-2i	99.2	+41.4
1j	“	28	(S)-2j	97.0	+32.6
1a	Rhodotorula glutinis	30	(R)-2a	99.0	−40.4
1b	“	30	(R)-2b	97.0	−38.7
1c	“	30	(S)-2c	95.3	−48.3
1d	“	30	(R)-2d	97.8	−19.7
1e	“	30	(R)-2e	98.0	−25.0
1f	“	30	(R)-2f	97.7	−34.9
1g	“	30	(R)-2g	94.2	−48.3
1h	“	30	(R)-2h	95.7	−48.3
1i	“	30	(R)-2i	98.0	−41.5
1j	“	30	(R)-2j	98.0	−32.6

^a18 h, 2 mmol of ketone/1.5 mL of EtOH was added to 15 g of yeast (wet weight)/400 mL of nutrient broth 1 (malt extract, peptone) for Geotrichum candidum or nutrient broth 2 (yeast extract, malt extract, peptone) for Rhodotorula glutinis. ^bee>99%. ^cSee Materials and Methods for c values and solvent.