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2004
Stereochemistry
O 0030
Desymmetrizing Hydroformylation with the Aid of a Planar Chiral CatalystGroup. — A desymmetrizing hydroformylation of prochiral bisalke50- 023 -Directing
nyl-carbinols (I) and bisallylcarbinols (VIII) employing a new planar chiral catalyst
directing group is reported. Thus, hydroformylation of (III) furnishes the syn-aldehyde
(V) as major product in good to excellent diastereoselectivity and in enantiomerically
pure form. Hydroformylation of (IX) gives the anti-aldehydes (X) in good yield, excellent syn/anti diastereoselectivity and in enantiomerically pure form. Removal and
recovery of the catalyst-directing group is achieved through saponification after protection of the aldehyde or alternatively, by reductive removal with DIBAL. —
(BREIT*, B.; BREUNINGER, D.; J. Am. Chem. Soc. 126 (2004) 33, 10244-10245;
Inst. Org. Chem. Biochem., Albert-Ludwigs-Univ., D-79104 Freiburg/Br., Germany;
Eng.) — Bartels
2004
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