Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates.
The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3-butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh(2)(S-BPTPI)(4), proceeded cleanly and gave, after treatment with acetyl chloride, the corresponding dihydropyranones in up to 99% ee.
Watanabe
Yudai
Y
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Washio
Takuya
T
Shimada
Naoyuki
N
Anada
Masahiro
M
Hashimoto
Shunichi
S
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
C546813:1-dimethylamino-3-silyloxy-1,3-butadiene; D000447:Aldehydes; D000588:Amines; D017646:Organosilicon Compounds; D012238:Rhodium