| Identification | Back Directory | [Name]
1-t-Butylthio-1-t-butyldimethylsilyloxyethylene | [CAS]
121534-52-9 | [Synonyms]
1-t-Butylthio-1-t-butyldimethylsilyloxyethylene
Silane, (1,1-dimethylethyl)[[1-[(1,1-dimethylethyl)thio]ethenyl]oxy]dimethyl- | [Molecular Formula]
C12H26OSSi | [MDL Number]
MFCD17013248 | [MOL File]
121534-52-9.mol | [Molecular Weight]
246.48 |
| Hazard Information | Back Directory | [Description]
1-t-Butylthio-1-t-butyldimethylsilyloxyethylene is an excellent reagent for Lewis acid-mediated aldol-type reactions, under either stoichiometric or catalytic conditions. | [Physical properties]
colorless liquid; bp 145°C/20 mmHg. | [Uses]
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. | [Preparation]
the reagent is obtained by reaction of tbutyl
thioacetate with lithium diisopropylamide in THF/HMPT
and subsequent trapping with t-butyldimethylchlorosilane
(75% yield). | [storage]
1-t-Butylthio-1-t-butyldimethylsilyloxyethylene should be stored in the absence of moisture at -15 °C. |
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