Mukaiyama aldol addition to α-chloro-substituted aldehydes. Origin of the unexpected syn selectivity.

• The addition of sterically demanding enolsilanes to alpha-chloro aldehydes results unexpectedly in preferential formation of the anti-PFA product (1,2-syn), while the addition of the corresponding boron enolate furnishes the expected polar Felkin-Anh product (1,2-anti). A stereoinduction model explaining these observations is proposed.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

ASYMMETRIC INDUCTION

1

3-ASYMMETRIC INDUCTION

ACYCLIC STEREOSELECTION

FELKIN-ANH

MODEL

ENOL

CONDENSATION

CORNFORTH

ENOLSILANES

GEOMETRY

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