84363-95-1Relevant academic research and scientific papers
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
Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols
Kimura, Masanari,Shimizu, Masamichi,Tanaka, Shuji,Tamaru, Yoshinao
, p. 3709 - 3718 (2007/10/03)
Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et 2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60-90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.
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.
Preparation of New Classes of Aliphatic, Allylic, and Benzylic Zinc and Copper Reagents by the Insertion of Zinc Dust into Organic Halides, Phosphates, and Sulfonates
Jubert, Carole,Knochel, Paul
, p. 5425 - 5431 (2007/10/02)
The insertion of zinc dust into primary alkyl chlorides, bromides, phosphates, and sulfonates in a polar solvent (DMPU, DMA) and in the presence of a catalytic amount of LiI (0.2 equiv) provides new organozinc reagents of the type RZnX (X = Cl, Br, OSO2R,
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
