By M. Santelli, J.-M. Pons
Using Lewis acids in natural synthesis, specifically in catalysis is likely one of the such a lot swiftly constructing fields in man made natural chemistry. moreover, Lewis acid catalysis is without doubt one of the key applied sciences for uneven synthesis, and combinatorial chemistry in addition to for large-scale production.
previously, pertinent info on those subject matters used to be scattered in the course of the literature. even supposing evaluation articles have appeared,it was once tough for the researcher to check various tools according to Lewis acids. This two-volume instruction manual, edited and written via a superb staff of specialists within the box, fills this gap!
This booklet relies on a class based on steel centre of those electron-deficient compounds, permitting an in-depth therapy of the features, merits and obstacles of every type of acid. vast cross-referencing and a accomplished index allows readers to speedy uncover the answer to their synthesis challenge. The chemical neighborhood will welcome this as a resource of idea and necessary reference for day-by-day paintings.
Chapter 1 creation (pages 1–7): Hisashi Yamamoto
Chapter 2 Li(I), Na(I), and K(I) Lewis Acids (pages 9–58): Susumu Saito
Chapter three Mg(II) and Zn(II) Lewis Acids (pages 59–88): Yukihiro Motoyama and Hisao Nishiyama
Chapter four Achiral B(III) Lewis Acids (pages 89–133): Kazuaki Ishihara
Chapter five Chiral B(III) Lewis Acids (pages 135–190): Kazuaki Ishihara
Chapter 6 Achiral Al(III) Lewis Acids (pages 191–281): Takashi Ooi and Keiji Maruoka
Chapter 7 Chiral Aluminum Lewis Acids in natural Synthesis (pages 283–354): William D. Wulff
Chapter eight Silicon(IV) Lewis Acids (pages 355–393): Masataka Oishi
Chapter nine Sn(II) and Sn(IV) Lewis Acids (pages 395–452): Kazuaki Ishihara
Chapter 10 coaching and Addition Reactions of Allylic and Allenic Tin and Indium Reagents (pages 453–522): James A. Marshall
Chapter eleven Sb(III) and Sb(V) Lewis Acids (pages 523–541): Kazuaki Ishihara
Chapter 12 Copper Lewis Acids in natural Synthesis (pages 543–574): Mukund P. Sibi and Gregory R. Cook
Chapter thirteen Ag(I), Au(I) Lewis Acids (pages 575–596): Akira Yanagisawa
Chapter 14 Transition steel Lewis Acids: From Vanadium to Platinum (pages 597–652): E. Peter Kundig and Christophe M. Saudan
Chapter 15 Titanium(IV) Lewis Acids (pages 653–798): Hirokazu Urabe and Fumie Sato
Chapter sixteen Chiral Ti(IV) Lewis Acids (pages 799–847): Koichi Mikami and Masahiro Terada
Chapter 17 Hf?Centered Lewis Acids in natural Chemistry (pages 849–864): Keisuke Suzuki and Shigeo Yamanoi
Chapter 18 Zirconium Lewis Acids (pages 865–881): Ryuichiro Hara and Tamotsu Takahashi
Chapter 19 Sc(III) Lewis Acids (pages 883–910): Shu Kobayashi
Chapter 20 Lanthanide Lewis Acids Catalysis (pages 911–944): Masakatsu Shibasaki, Ken?Ichi Yamada and Naoki Yoshikawa
Chapter 21 Polymer?Supported steel Lewis Acids (pages 945–979): Shinichi Itsuno
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Additional info for Lewis Acids in Organic Synthesis
It is reasonable to ascribe this to a decrease in congestion in monomers relative to open dimers. Indeed, for metallation of imine 2 with LDA in THF (4 must be a real species) the rate behavior was consistent with the mechanism specified by M-1. When 2:2 TMEDA-LDA complex 1 was used for deprotonation of 3, a solvent-free open dimer proved to be a plausible reactive intermediate (Sch. 5 ) . Accordingly, the rate of imine metalation depends strongly on the solvent and substrate used . Kinetic evidence obtained in the enolization experiment with sterically demanding ester 5 showed disolvated LDA monomers to be the reactive form, providing the first direct support for Ireland’s hypothesis of cyclic transition state structures in LDA-mediated enolizations (Sch.
Although a four-center transition state M-2 involving the monomer has long been believed to participate in the alkylation , some ab initio calculation evidence shows that an open dimer OD-2 or related dimeric structure is more likely to be involved in the reactions, especially when (MeLi)2 participates [35, 361. McGarrity and co-workers showed that the dimer of n-BuLi is tenfold more reactive than the tetramer toward benzaldehyde in THE Even at high dilution there is no detectable concentration of the monomer .
Subsequent results implied, however, that LiBF4 functioned as a slow-releasing source of BF3, rather than working as a cationic lithium species . O mol% CSA rt. H. 61 Scheme 29 For some reason a$-unsaturated ketones are less reactive species as dienophiles. 0 mol YO CSA. 0 M LPDE or CSA consistently furnished ketals only. Note that cycloadditions readily occur ar room temperature and 0 "C in contrast to the low temperatures required under Gassman conditions (2 mol % TfOH, CH2C12-Cl2FCCFzC1, -78 "C).