128373-69-3

Upstream product

• 128373-65-9 (4S),(Z)-1-benzyloxy-4,5-(isopropylidenedioxy)-2-pentene 
• 80532-35-0 (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 
• 100-39-0 benzyl bromide 
• 81703-94-8 methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 
• 128373-67-1 (2S),(Z)-5-benzyloxy-3-pentene-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

STEREOSELECTIVE SN2' ADDITIONS OF ORGANOCUPRATES TO HOMOCHIRAL ACYLIC VINYLOXIRANES

Additions of various methylcopper reagents to the homochiral acylic vinyloxiranes A14, A15, B6-B9, and C5, C6 were performed in order to evaluate E/Z and syn/anti preferences.The unsubstituted oxiranes A14 and A15 gave a mixture of SN2 and SN2' substitution products with the four reagents examined, LiMe2Cu, LiMeCuCN, BrMgMe2Cu, and LiMeCuI*BF3.The more highly substituted systems B6-B9 derived from geraniol and C5, C6 derived from nerol yielded only SN2' products.The (Z)-allylic alcohol derivatives B8 and C6 and LiMeCuCN gave the best anti/syn ratios (99:1 and 97:3, respectively).In both cases the newly formed double bond was exclusively E.