111427-78-2Relevant academic research and scientific papers
Silicon-Directed Stereoselective Synthesis of 2-vinyl-1,3-diols. Stereo-Divergence with and without the silyl Group Related to the Synthesis of Avenaciolide and Isoavenaciolide
Suzuki, Keisuke,Miyazawa, Mayumi,Shimazaki, Masato,Tsuchihashi, Gen-ichi
, p. 4061 - 4072 (2007/10/02)
A flexible approach to the stereoisomers of 2-vinyl-1,3-diols via the reduction of 2-vinyl aldols is described.The presence of the TMS group at the α-position of the vinyl group firmly establishes the syn relationship between the newly-formed hydroxyl gro
CATALYTIC VERSION OF EPOXY SILYL ETHER REARRANGEMENTS
Suzuki, Keisuke,Miyazawa, Mayumi,Tsuchihashi, Gen-ichi
, p. 3515 - 3518 (2007/10/02)
Catalytic version of epoxy silyl ether rearrangements using Me3SiX (X=I, OTf: 5 molpercent) as the Lewis acid catalyst is reported, which leads to generally higher yields of the aldol products than stoichiometric version.
SYNTHESIS OF 2-VINYL-1,3-DIOLS VIA HIGHLY STEREOSELECTIVE REDUCTION OF 2-VINYL ALDOLS USING TRIMETHYLSILYL STEREO-DIRECTING GROUP
Suzuki, Keisuke,Shimazaki, Masato,Tsuchihashi, Gen-ichi
, p. 6233 - 6236 (2007/10/02)
Stereo-defined 2-vinyl-1,3-diols are synthesized by the reduction of aldol derivatives bearing α-trimethylsilylvinyl group at C(2) (LiBEt3H/THF, -78 deg C), which proceeds highly stereoselectively to give 1,2-syn isomer as the sole product.
STEREO-DIVERGENT ASYMMETRIC TOTAL SYNTHESIS OF AVENACIOLIDE AND ISOAVENACIOLIDE. COMPLETE REVERSAL OF STEREOSELECTIVITY IN REDUCTION OF 2-VINYL ALDOLS WITH / WITHOUT TRIMETHYLSILYL DIRECTING GROUP
Suzuki, Keisuke,Miyazawa, Mayumi,Shimazaki, Masato,Tsuchihashi, Gen-ichi
, p. 6237 - 6240 (2007/10/02)
Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide was achieved via 1,2-rearrangement of chiral epoxyalcohol derivatives, where complete reversal of stereoselectivity with / without the TMS-directing group in the reduction of
