By Mary Fieser
This ongoing sequence, originated in 1967, has turn into the traditional advisor to the practise, houses and makes use of of hundreds of thousands of reagents, and extra references to reagents formerly mentioned. It contains information on structural formulae, molecular weight, actual constants, most popular approach to education, and examples of significant makes use of. It additionally comprises facts on widely used reagents from 1966 to 1988.
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Extra info for Fieser And Fieser's Reagents for Organic Synthesis (Volume 14)
Hamano, (1). ,80" 604s% NHt NH, H form unc! 1 Asymmetriclactonization2 The diamide3, preparedfrom (R)-1 and 2, on treatment with TFA is convertedinto the 8-lactone4 in 98Vode by a highly diastereoselective reactionwith the pro-S-carbonylgroup of 3. :, . - ;cHoH cFlcooH, cHrclr, -20.. r 1988). O,py 2) LiBH. ). Hll o 4 gSVo de\ O O 5 (98Vo ee) However,similarcyclizationof the relateddiamide6 resultsin the 1-lactonez, formed with moderatediastereoselectivity with the pro-R carbonyl group. The unexpectedasymmetricbias is ascribedto the highly straineddiamidering of 6.
Tanaka,Tetrahedron (1988). Letters,29,55l Bis(pentamethylcyclopentadienyl)dimethyltitanium(IV),(CsMe')zTi(CHr)'. In the caseof cyclohexeneoxide, the product is a titanium enolateof (equaBut the enolatesformed by reactionwith 1,2-epoxybutane cyclohexanone. (Equation differ from thoseformed from 2-butanone tion I) or 2,3-epoxybutane to the II). Apparentlythe reactionwith epoxidesdoesnot involverearrangement of hytransfer ketone but complexationof the epoxide oxygen to the metal and drogen from the substrateto the methylenegroup.
And 6for high enantioselectivity. l2Vo ofthe tartrategenerallyproceedin high conversionand high enantioselectivity (90-95Voee). Some increasein the amount of catalystcan increasethe enantioselectivityby l-5Vo, but can complicateworkup and lower the yield. to 50-100 mole Vocan even lower the enantioselectivity. The product was usedfor an enantioselective e r t c di n t o r l . Igents -l'hcv are 1 'vr6 ). t triple < r '; v i e l d n hcnzene. This epoxroute to venustatriol,a tetraoxacyclic epoxidationof a trishomoallylicalcohol.
Fieser And Fieser's Reagents for Organic Synthesis (Volume 14) by Mary Fieser