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.
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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.