Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by the chiral phosphine oxide BINAPO

Synlett

Volumn , Issue 7, 2006, Pages 1116-1118

  Kotani, Shunsuke ^a   Hashimoto, Shunichi ^b   Nakajima, Makoto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Asymmetric catalysis; Lewis bases; Phosphine oxides; Stereoselectivity

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; TRICHLOROSILYL ENOL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY;

EID: 33646557046     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939725     Document Type: Article

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49. E-Enol ether (E/Z, >20:1): 96% yield, syn/anti, 1:25, 28% ee(syn), 12% ee(anti); Z-enol ether (E/Z, 1:4): 92% yield, syn/anti, 3.8:1, 31% ee(syn), 13% ee(anti).
50. 4, and concentrated. The crude material was purified by column chromatography (silica gel, 5 g, hexane-EtOAc, 6:1) to give the adduct as a syn/anti mixture (85 mg, 90% yield). Stereoselectivities were determined by HPLC (Chiralpak AD-H, hexane-i-PrOH, 4:1).