84363-95-1Relevant articles and documents
Stereospecificity in the Lewis acid promoted allylation reaction of 3,3- disubstituted allyltins toward aldehydes
Nishigaichi, Yutaka,Takuwa, Akio
, p. 109 - 112 (1999)
The Lewis acid-promoted reaction of 3,3-disubstituted allyltins toward aldehydes was found to be stereospecific; the (E)-reagent gave syn-products and the (Z)-one gave anti-products. This is in contrast to that of 3-mono- substituted congeners which are k
Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes
Nowotny, Stefan,Tucker, Charles E.,Jubert, Carole,Knochel, Paul
, p. 2762 - 2772 (2007/10/02)
The addition of γ-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of γ-monosubstituted allylchromium(III) species.The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the α-position.The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors.The reaction has been extended to a γ-monosubstituted β-(trimethylsilyl)allylic system.The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.
STEREOSELECTIVE ACYCLIC SYNTHESIS VIA ALLYLMETALS: STRUCTURAL DEPENDENCE IN A LEWIS-ACID CATALYZED ADDITION OF ALLYLTINS TO ALDEHYDES
Koreeda, Masato,Tanaka, Yoshio
, p. 1299 - 1302 (2007/10/02)
Lewis-acid catalyzed reaction of allyltins with aldehydes at -78 deg C provide homoallyl alcohols with high stereoselectivity; 2-alkenyltins in general provide erythro adducts preferentially with an erithro/threo ratio greater than 12/1, whereas only thre