A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction.
The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used.
Shinoyama
Mariko
M
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
Shirokawa
Shin-ichi
S
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D010080:Oxazoles; D012821:Silanes; C116609:3-hydroxybutanal