53847-16-8Relevant academic research and scientific papers
Conjugate allylation to α,β-unsaturated aldehydes with amphiphilic alkylation system, ATPH/allylcerium reagents
Ooi, Takashi,Miura, Tomoya,Kondo, Yuichiro,Maruoka, Keiji
, p. 3947 - 3950 (1997)
Conjugate allylation to α,β-unsaturated aldehydes has been successfully accomplished with a new amphiphilic alkylation system, aluminium tris(2,6-diphenylphenoxide) (ATPH)/allylcerium reagents. Diallylcerium chloride was found to be the most satisfactory
How an early or late transition state impacts the stereoselectivity of tetrahydropyran formation by intramolecular oxa-Michael addition
Bates, Roderick W.,Csókás, Dániel,Ho, Annabel Xuan Ying,Ramabhadran, Raghunath O.
supporting information, p. 6293 - 6304 (2019/07/03)
The intramolecular oxa-Michael addition giving tetrahydropyrans has been examined experimentally using both acidic and basic catalysis. With acidic catalysis, the diequatorial product is exclusively obtained in a kinetically controlled reaction in all cas
DABO Boronate Promoted Conjugate Allylation of α,β-Unsaturated Aldehydes Using Copper(II) Catalysis
Roest, Pjotr C.,Michel, Nicholas W. M.,Batey, Robert A.
, p. 6774 - 6778 (2016/08/16)
The first catalytic method for the selective 1,4-conjugate allylation of α,β-unsaturated aldehydes is reported. The method employs an air-stable diethanolamine-complexed boronic acid (DABO boronate) as the allyl transfer reagent and promotes conjugate add
Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation
Pandiancherri, Shveta,Lupton, David W.
, p. 671 - 674 (2011/03/22)
Exposure of N-chloroamines to KOtBu or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of π4s + π2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines.
Synthesis of cyclic ethers utilizing a cyclization-fragmentation strategy
Ockey, Denise A.,Lane, David R.,Seeley, Juliette A.,Schore, Neil E.
, p. 711 - 717 (2007/10/03)
A variety of cyclic ethers have been prepared via both solution phase and polymer-supported sequences of 3 + 2 cycloaddition of nitrile oxides to alkenes and dienes to give isoxazolines, followed by electrophile-induced cyclization. Library generation by
Phosphazene bases and the anionic oxy-Cope rearrangement
Mamdani, Hassan T.,Hartley, Richard C.
, p. 747 - 749 (2007/10/03)
Compounds containing a 1,5-hexadien-3-ol system undergo anionic oxy-Cope rearrangement when treated with the phosphazene super-base, P4-t-Bu. The [3,3] sigmatropic rearrangement occurs in hexane as well as in THF. The weaker phosphazene base, P
The first example of asymmetric induction in an anionic amino-Cope rearrangement
Allin, Steven M.,Button, Martin A. C.
, p. 3345 - 3348 (2007/10/03)
The anionic amino-Cope rearrangement of suitably functionalized acyclic 3-amino-1,5-diene substrates has been achieved and we report the first example of an asymmetric anionic amino-Cope rearrangement to yield an enantiomerically enriched product (75% e.e.). The absolute stereochemistry of the products has been verified and transition state models are proposed to rationalize the stereochemical outcome.
Regioselective addition reaction of organolanthanide reagents to α,β-unsaturated imines
Qian, Changtao,Huang, Taisheng
, p. 143 - 147 (2007/10/03)
Organolanthanum reagents[RLaCl2] generated in situ from LaCl3 and alkyl lithium or allyl magnesium could undergo a highly regioselective 1,2-addition to N-alkyl α,β-unsaturated imines, which provided a new and useful approach to synthesize allyl amines with good yields and high regioselectivity. Furthermore, for N-chiral alkyl α,β-unsaturated imine, in the case of n-butyl lithium, the diastereoselectivity achieved highly 90%.
Conjugate allylation to α,β-unsaturated aldehydes with the new chemzyme p-F-ATPH
Ooi,Kondo,Maruoka
, p. 1183 - 1185 (2007/10/03)
Success at last: The 1,4-allylation of α,β-unsaturated aldehydes with selectivities up to 95/5 and yields of 83% has been achieved thanks to the newly developed Lewis acidic receptor p-F-ATPH (L= 2,6-(p-FC6H4)2C6H3O). In addition to a coordination site for the aldehyde, this possesses an appropriate coordination site for a reactive nucleophile, as shown schematically on the right.
