Interestingly, 2b, obtained by deprotonation of optically
active (1S,2R)-(+)-1-phenylpropylene oxide 1b,
proved to be more reactive with respect to the trans
isomer 2a and configurationally stable. Under the same
conditions as above, the deprotonation of 1b, at -98 °C,
required only 30 min for completion, and the corresponding
oxiranyllithium 2b was quantitatively deuterated
(> 98% D) with complete retention of configuration at
the R-carbon (Table 2)