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

Mukaiyama aldol addition to alpha-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 expla...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2010-01, Vol.46 (8), p.1281-1283
Hauptverfasser: Borg, Tessie, Danielsson, Jakob, Somfai, Peter
Format: Artikel
Sprache:eng
Schlagworte:
3-ASYMMETRIC INDUCTION
ACYCLIC STEREOSELECTION
ASYMMETRIC INDUCTION
CONDENSATION
CORNFORTH
ENOL
ENOLSILANES
FELKIN-ANH
GEOMETRY
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/b922954j