Silicon-mediated olefination Flashcards

1
Q

Which are more reactive - alpha-silyl carbanions or phosphorus-stabilised anions?

A

Alpha-silyl. Particularly useful for sterically hindered carbonyls (when Wittig reagent fails)

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2
Q

Describe outcome of B-hydroxysilane elimination

A

Undergo under basic and acidic conditions. Stereochemical outcome (E/Z) depends on conditions and stereochemistry of starting B-hydroxysilane.

Base-mediated: requires synperiplanar, eclipsed
Acid-mediated: antiperiplanar, staggered

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