TY - JOUR
T1 - (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary
T2 - A new strategy for the asymmetric synthesis of 2-substituted alcohols
AU - Clayden, Jonathan
AU - McCarthy, Catherine
AU - Cumming, John G.
PY - 1998/4/24
Y1 - 1998/4/24
N2 - The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along-with the (S)-2- (dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols beating oxygen- or carbon-based 2-substituents.
AB - The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along-with the (S)-2- (dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols beating oxygen- or carbon-based 2-substituents.
UR - http://www.scopus.com/inward/record.url?scp=0032562768&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(98)00120-7
DO - 10.1016/S0957-4166(98)00120-7
M3 - Article (Academic Journal)
AN - SCOPUS:0032562768
SN - 0957-4166
VL - 9
SP - 1427
EP - 1440
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
IS - 8
ER -