121534-52-9

1-t-Butylthio-1-t-butyldimethylsilyloxyethylene is an excellent reagent for Lewis acid-mediated aldol-type reactions, under either stoichiometric or catalytic conditions.

colorless liquid; bp 145°C/20 mmHg.

1-t-Butylthio-1-t-butyldimethylsilyloxyethylene is a excellent reagent for Lewis acid-mediated aldol-type reactions, under either stoichiometric3c?e or catalytic conditions.
The reagent undergoes Lewis acid-catalyzed Mukaiyama-type additions to aldehydes to give β-hydroxy thioesters with good yields and remarkable enantioselectivity (eq 1).Slow addition of the aldehyde (3–20 h) is necessary for high enantioselectivity.

the reagent is obtained by reaction of tbutyl thioacetate with lithium diisopropylamide in THF/HMPT and subsequent trapping with t-butyldimethylchlorosilane (75% yield).

1-t-Butylthio-1-t-butyldimethylsilyloxyethylene should be stored in the absence of moisture at -15 °C.