Stereoselective synthesis of secondary organozinc reagents and their reaction with heteroatomic electrophiles.

[figure: see text] Various trisubstituted olefins were converted to configurationally stable diorganozinc compounds with high diastereoselectivity. Their reaction with various electrophiles centered on tin, sulfur, bromine, and phosphorus provided the desired substitution products with retention of configuration. Novel, functionalized organocopper reagents such as 4 and chiral diphosphine 5 have been prepared.