19947-22-9Relevant articles and documents
Short synthesis of chiral 4-substituted (S)-imidazolinium salts bearing sulfonates and their use in γ-selective reactions of allylic halides with grignard reagents
Latham, Christopher M.,Blake, Alexander J.,Lewis, William,Lawrence, Matthew,Woodward, Simon
supporting information; experimental part, p. 699 - 707 (2012/03/11)
A one-pot reaction of Boc-protected amino alcohols and 2-sulfobenzoic anhydride followed by the addition of a wide variety of primary amines has allowed rapid access to diverse libraries of amidosulfonates 1,2-C 6H4(SO3su
Direct copper-free domino conjugate addition-cycloallylation using organozinc reagents
Komanduri, Venukrishnan,Pedraza, Fernando,Krische, Michael J.
supporting information; experimental part, p. 1569 - 1576 (2009/07/30)
The Direct Approach: Enones possessing appendant allylic carbonates react directly with diorganozinc reagents in the presence of zinc diiodide [ZnI 2] to provide 5- and 6-membered ring products of tandem or domino conjugate addition-cycloallylation in good to excellent yield. In a related copper-free transformation, allylic carbonates are found to engage in direct allylic substitution with diorganozinc reagents.
Studies of the formation of all-carbon quaternary centres, en route to lyngbyatoxin A. A comparison of phenyl and 7-substituted indole systems.
Tonder, Janne E,Hosseini, Masood,Ahrenst, Alex B,Tanner, David
, p. 1447 - 1455 (2007/10/03)
Copper mediated allylic substitutions and conjugate additions to geranyl, cinnamyl and allylic indole compounds have been investigated with the aim of finding a method for the creation of the all-carbon quaternary centre present in the natural product lyngbyatoxin A. Reaction conditions have been found giving a 68% SN2' selectivity in the copper mediated addition of PhMgBr to geranyl chloride, as well as 99% and 95% SN2' selectivity in the copper catalysed addition of EtMgBr to cinnamyl chloride and acetate, respectively. When the optimised reaction conditions were applied to the corresponding allylic compounds containing a 7-substituted indole moiety, the regioselectivity was reversed giving only the SN2 product. The allylic indole-containing substrates were also found to be unproductive in Pd- or Mo-catalysed SN2'-type substitution reactions. In related studies, copper catalysed conjugate addition of EtMgBr to the tricyclic lactam 6-methyl-pyrrolo[3,2,1-ij]quinolin-4-one gave a maximum of 20% of the 1,4-addition product.
