Table 3.

Aldol Reaction of Racemic Formylphosphinate Hydrate and Ketones^a

entry	6		catalyst	10 and 11	time (h)	yield (%)b	10/11c	syn/antid	ee (%)e
	R1	R2							syn-10	syn-11	anti-10	anti-11
1f	H	H	4	a	24	0	---	---	---	---	---	---
2f	H	H	1	a	1.5	89	50:50	---	90g	79g	---	---
3	H	H	1	a	7	91	50:50	---	93g	87g	---	---
4f	-(CH2)2-		1	b	24	79	50:50	>99:1	97	62	---	---
5	-(CH2)2-		1	b	30	83	50:50	99:1	96	87	---	---
6	-(CH2)3-		1	c	32	88	50:50	35:65	98h	95h	89h	93h
7	-(CH2OCH2)-		1	d	30	91	50:50	40:60	99h	94h	26h	99h

^aUnless otherwise indicated, all reactions were carried out with the racemic formylphosphinate hydrate (0.50 mmol) in dry ketone (0.5 mL) with the catalyst (0.10 mmol, 5 mol %) for the specified reaction time at 0 °C.

^bTotal yield of the inseparable diastereomers (10 and 11) isolated after column chromatography.

^cDetermined by ¹H NMR analyses; the value refers to the ratio of the products containing R_P and S_P stereochemistry.

^dDetermined by ¹H NMR analyses, syn and anti refer to the stereochemistry of the two newly generated carbon stereogenic centers.

^eEnantioselectivity was determined by HPLC analyses.

^fThe reaction was carried out at room temperature.

^gThis compound does not has syn or anti stereochemistry.

^hThe assignments of the ee values to the structures are arbitrary in these cases. Due to partial overlaps of some of the peaks, the error limit of the ee values is considerably larger than normal.