Table 2.

Syntheses of (E)-δ-Silyl-anti-homoallylic Alcohols 6^a

entry	RCHO	product	yieldb	% eec
1	PhCHO	6a	85%	95
2d	PhCHO	ent-6a	82%	94
3	PhCH=CHCHO	6b	78%	95
4	Ph(CH2)2CHO	6c	89%	93
5	CyCHO	6d	71%	94
6	TBSO(CH2)2CHO	6e	72%	95
7	BnOCH2CHO	6f	75%	96

^aReactions were performed by treating (±)-4 with (^dIpc)₂BH (1 equiv) in toluene at −25 °C and warming to −15 °C over 8 h followed by the addition of RCHO (0.45 equiv) at −78 °C. The mixture was then allowed to stir at −78 °C for 12 h. The reactions were subjected to a standard workup (NaHCO₃, H₂O₂) at 0 °C prior to product isolation.

^bBased on the amount of the aldehydes used in the crotylboration reaction.

^cDetermined by Mosher ester analysis.⁹

^d(^lIpc)₂BH was used for the hydroboration reaction.