Table 1.

Highly diastereo- and enantioselective one-pot aldehyde allylation and crotylation reactions with diaminophenol 6

entry	silane	RCHO	product	yield (%)a	dr	ee (%)
1	9			83	-	> 99
2	9			81b	-	98
3	10c			94b	98:2d	96
4	11e			88	94:6d	97
5	10c			92	> 98:2d	93
6	9			82	98:2f	-
7	10c			82	92:8g	-
8	11e			80	93:7g	-
9	9			80	98:2f	-
10	10c			80	94:6g	-
11	11e			80	95:5g	-
12	9			87b	96:4f	-

^aIsolated yield of purified products.

^bA modified workup and isolation procedure was employed.

^cThe geometric purity of the cis-crotyltrichlorosilane employed was measured to be >99:1 by ¹H NMR spectroscopic analysis.

^dSyn:anti diastereoselectivity as measured by ¹H NMR spectroscopic analysis.

^eThe geometric purity of the trans-crotyltrichlorosilane employed was measured to be 95:5 by ¹H NMR spectroscopic analysis.

^fAldehyde diastereoface selectivity as measured by ¹H NMR spectroscopic analysis.

^gRatio of the major diastereomer to the sum of the minor diastereomers as measured by HPLC and ¹H NMR spectroscopic analysis. See the supporting information for details.