Six-Membered Transition States in Organic Synthesis by Jaemoon Yang

By Jaemoon Yang

This booklet furthers readers’ knowing of the superb beneficial properties of 6-membered transition states in stereoselective natural reactions. accomplished and logically geared up, it covers reactions categorised in 4 different types: [3,3]-sigmatropic rearrangements, aldol reactions, steel allylation reactions, and stereoselective discount rates. there's a thorough dialogue of every response classification, in addition to computational reports that aid a suggestion of a 6-membered nation. The publication assists professors, researchers, and scholars in providing average transition states for the outline of newly stumbled on stereoselective reactions.

Show description

Read or Download Six-Membered Transition States in Organic Synthesis PDF

Best organic chemistry books

Biochemistry (6th Edition)

Become aware of how the newest advancements in biotechnology, genomics, and proteins at once have an effect on your lifestyles with Campbell/Farrell? s best-selling biochemistry textual content. recognized for its logical association and applicable intensity of insurance, BIOCHEMISTRY, 6th variation, balances medical element with clarity that?

Organic reaction mechanisms

Presents the latest advancements in natural chemistry. Compiled by means of well-respected editors with decades of correct event.

Microwaves in Organic Synthesis

The lengthy awaited re-creation of this entire two-volume reference has been thoroughly up to date and extended through 30% to incorporate chapters on ionic beverages, carbohydrate chemistry, multicomponent reactions, stable part peptide synthesis, carbon nanotubes and fullerenes. Written through the main eminent scientists of their respective fields, the chapters, which enhance each other, now additionally comprise 8 new fields of software, similar to heterocyclic chemistry, cycloadditions and carbohydrate chemistry.

Additional resources for Six-Membered Transition States in Organic Synthesis

Sample text

LiAlH4 H 3. 2f O HO H H 2. ClCO2Me, pyridine (90%) O O OH 1. 1 equiv) (83%) 12 CO2Me CO2Me 1. 25% aq. AcOH 2. ) O MeO2C TBSO 18 19 (70%) AD-mix β O O O O 1. TBAF, THF (84%) 2. MsCl, pyridine (90%) O TBSO 21 HO HO O 3. 2h was accessed by the same reaction sequence as that for the conversion of 6 to 7, afforded squalene upon treatment with isopropylidenetriphenylphosphorane in 36% yield. 2g). The first Johnson–Claisen rearrangement was carried out by heating the allylic alcohol 12, derived from 2,3-isopropylidene-L-erythrose (11), with trimethyl orthoacetate to afford the unsaturated ester 13 with an (E )-geometry.

Christ, W. ; Kishi, Y. J. Am. Chem. Soc. 1986, 108 , 5644. 3. Ireland–Claisen Rearrangement In 1976, Ireland et al. reported that [3,3]-sigmatropic rearrangement of allylic esters as enolate anions or corresponding silylketene acetals produces the γ,δ- unsaturated acids in good yields and with excellent levels of diastereoselectivity. 3a). 3b). An examination of nonbonded interactions readily indicates which of the two possible transition states will be favored. The equatorial disposition of the R group puts transition state A at lower energy, which results in predominant formation of the E -isomer.

Srebnick, M. Aldrichimica Acta 1993, 26, 17. 4. Ireland, R. ; Wilcox, C. S. J. Am. Chem. Soc. 1980, 102 , 1155. 5. Ireland, R. ; Anderson, R. ; Fitzsimmons, B. ; McGarvey, G. ; Wilcox, C. S. J. Am. Chem. Soc. 1983, 105 , 1988. 6. Still, W. ; Schneider, M. J. J. Am. Chem. Soc. 1977, 99 , 948. 7. (a) Grieco, P. ; Gilman, S. J. Org. Chem. 1980, 45 , 3537; (b) Martinez, G. ; Grieco, P. ; Srinivasan, C. V. J. Am. Chem. Soc. 1982, 104 , 1436. 8. Kim, H. ; Toogood, P. L. Tetrahedron Lett. 1996, 37 , 2349.

Download PDF sample

Rated 4.72 of 5 – based on 39 votes