Table 1.

syn-Diastereo- and enantioselective carbonyl crotylation from the alcohol oxidation level.^a

Entry	Product	Ligand	Yield [%]	ee [%]	syn:anti
1		A	81	87	13:1
2		A	87	90	≥20:1
3		A	84	90	≥20:1
4		B	85	90	≥20:1
5		B	70b	90	11:1
6		A	67b,c	90	≥20:1
7		A	70b	92	≥20:1
8		A	64b,c	86	≥20:1
9		A	65b,c,d	88	≥20:1
10		A	66	86	≥20:1

^aLigand A = (R)-DM-SEGPHOS, Ligand B = (R)- SEGPHOS. Yields are of isolated material. Diastereoselectivity was determined through ¹H NMR analysis of crude reaction mixtures. Enantiomeric excess was determined by chiral stationary phase HPLC analysis. See Supporting Information for details.

^b250 mol% 1.

^cTHF

^d7 mol% catalyst.