- PERFUME SYSTEM FOR PERFUMED CONSUMER PRODUCT
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The present invention relates to a perfume system comprising a core-shell microcapsule A, optionally, a core-shell microcapsule B, and optionally, a free perfume oil, wherein the core of the core-shell microcapsule A and/or the free perfume oil comprises a 2-oxoacetate derivative of formula (I) as well as a perfumed consumer product comprising the same and methods and uses of the same for enhancing, conferring, increasing and/or modifying the fragrance properties and/or the fragrance intensity of perfumed consumer products.
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Page/Page column 24; 25
(2021/10/30)
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- Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study
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Gold(I)-catalysed direct allylic etherifications have been successfully carried out with chirality transfer to yield enantioenriched, γ-substituted secondary allylic ethers. Our investigations include a full substrate-scope screen to ascertain substituent effects on the regioselectivity, stereoselectivity and efficiency of chirality transfer, as well as control experiments to elucidate the mechanistic subtleties of the chirality-transfer process. Crucially, addition of molecular sieves was found to be necessary to ensure efficient and general chirality transfer. Computational studies suggest that the efficiency of chirality transfer is linked to the aggregation of the alcohol nucleophile around the reactive π-bound Au-allylic ether complex. With a single alcohol nucleophile, a high degree of chirality transfer is predicted. However, if three alcohols are present, alternative proton transfer chain mechanisms that Erode the efficiency of chirality transfer become competitive.
- Barker, Graeme,Johnson, David G.,Young, Paul C.,Macgregor, Stuart A.,Lee, Ai-Lan
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p. 13748 - 13757
(2015/09/22)
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- Suzuki-Miyaura cross-couplings of secondary allylic boronic esters
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Palladium-catalyzed cross-coupling reactions of secondary allylic boronic esters with iodoarenes were demonstrated under the conditions previously described for the coupling of benzylic substrates. The regioselectivity of the process was largely dictated by the pattern of olefin substitution. The Royal Society of Chemistry 2012.
- Glasspoole, Ben W.,Ghozati, Kazem,Moir, Jonathon W.,Crudden, Cathleen M.
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supporting information; experimental part
p. 1230 - 1232
(2012/02/15)
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- Pd(II)-catalyzed aliphatic Claisen rearrangements of acyclic allyl vinyl ethers
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Palladium (II)-catalyzed [3,3] sigmatropic rearrangement of acyclic allyl vinyl ethers delivers 2,3-anti disubstituted pentenal Claisen adducts with high diastereoselectivity. Reaction conditions for circumventing allyl vinyl ether cleavage that had previ
- Kerrigan, Nessan J.,Bungard, Christopher J.,Nelson, Scott G.
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p. 6863 - 6869
(2008/12/20)
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- Synthesis of vinyl 1,2-diketones
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A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by 1O2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones.
- Habel, Lothar W.,De Keersmaecker, Sigrid,Wahlen, Joos,Jacobs, Pierre A.,De Vos, Dirk E.
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p. 4057 - 4059
(2007/10/03)
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- Acid-catalyzed rearrangement of α-hydroxytrialkylsilanes
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Cationic rearrangement of several α-hydroxysilanes is described. Treatment of both (1R,1′R,2′S)-α-hydroxycyclopropylsilane syn-9 and (1S,1′R,2′S)-anti-9 under aqueous H2SO4 underwent rearrangement via a common α-silyl cation intermediate A to give a mixture of the ring-opened (R)-vinylsilane 13, the tandem [1,2]-CC bond migration product (1R,2S,1′R)-14, and its 1′S isomer 15. On the other hand, the acidic treatment of (R,E)-α-hydroxyalkenylsilane 8 or (R,Z)-8 was each accompanied with partial racemization to give an enantiomeric isomer of allylic alcohol 23 via a preferential syn-facial SN2′ reaction, respectively. Both α-hydroxyalkynylsilane 6 and α-hydroxyalkylsilane 12 were inert to the acidic conditions; however, treatment of (R)-α-mesyloxyalkynylsilane 26 under aqueous H2SO4 gave a mixture of the optically active rearranged allene 27, α,β-unsaturated ketone 28, and (S)-α-hydroxyalkynylsilane 6 with partial racemization. Comparisons of the reactivities of these α-hydroxysilanes under acidic conditions are also disclosed.
- Sakaguchi, Kazuhiko,Higashino, Masato,Ohfune, Yasufumi
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p. 6647 - 6658
(2007/10/03)
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- Stereoselective reactions of acyclic allylic phosphates with organocopper reagents
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A series of acyclic allylic alcohols of general structure R1CH=CHCH(OH)R2 were resolved by Sharpless kinetic resolution. The hydroxyl groups of these enantiomerically enriched alcohols were derivatized to diethyl phosphates, and the derivatives were reacted with organocopper reagents. Cleanest substitution reactions were observed with reagents R32CuCNLi2. With R1 = Me and R3 = n-Bu, the size of R2 affected both the regioselectivity and stereoselectivity of the displacement. Larger R2 groups gave higher regio- and stereoselectivities: with R2 = 3-pentyl, >98% SN2′ regioselectivity and > 98% anti stereoselectivity were observed. Bn2CuCNLi2 gave stereoselectivities comparable to those observed with n-Bu2CuCNLi2 but t-Bu2CuCNLi2 exhibited much lower diastereofacial preference.
- Belelie,Chong
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p. 5552 - 5555
(2007/10/03)
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- The regioselective 1,4-addition reaction of alkenylboronic acids to α,β,α′,β′-unsaturated ketones
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The effect of substituents on the double bond of α,β-unsaturated ketones for the 1,4-addition reaction rate of alkenylboronic acids induced by cyanuric fluoride was studied in detail. When the steric hindrance around the β-carbon of the unsaturated ketones increased, the 1,4-addition reaction rate significantly decreased. An alkyl substituent on the α-carbon was also found to significantly affect the 1,4-addition reaction. From these results, unsymmetric α,β,α′,β′unsaturated ketones (10a-f) were designed for the regioselective 1,4-addition reaction with alkenylboronic acids (4a-j). Since they have substituents to disturb the 1,4-addition reaction on only one double bond, the alkenylboronic acids reacted with them from only one side to selectively provide γ,δ,α′,β′-unsaturated ketones (11a-q). Further transformations of the resulting γ,δ,α′,β′-unsaturated ketones were also performed.
- Hara, Shoji,Shudoh, Hisashi,Ishimura, Shigeyuki,Suzuki, Akira
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p. 2403 - 2408
(2007/10/03)
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- A Highly Regioselective Reaction of Allylic Acetates with Silylated Carbon Nucleophiles Directed by a Sulfenyl Group. Scope, Limitation, and Mechanistic Aspects
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α-(Sulfenylmethyl)allyl acetates reacted with silylated carbon nucleophiles in the presence of a catalytic amount of TMSOTf to give products substituted at the α-position of the sulfenylmethyl group in moderate to good yields with high regioselectivity.The theoretical calculation on an intermediate cationic species indicated that an episulfonium ion was a stable form; the observed regioselectivity was rationalized qualitatively on the basis of the coefficients of LUMO of the cation.Some transformations of the products were also demonstrated.
- Kudo, Kazuaki,Hashimoto, Yukihiko,Houchigai, Hitoshi,Hasegawa, Masaki,Saigo, Kazuhiko
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p. 848 - 856
(2007/10/02)
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- On the Mechanism of Organoaluminum-Promoted Claisen Rearrangement of Allylic Vinyl Ethers
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The organoaluminum-promoted Claisen rearrangement of allylic vinyl ethers has been mechanistically studied by two sets of experiments and the observed Z and E selectivity is best accounted for by two possible chair-like structures with R substituents axial and equatorial, respectively.
- Nonoshita, Katsumasa,Maruoka, Keiji,Yamamoto, Hisashi
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p. 541 - 545
(2007/10/02)
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- THE REACTION OF α,β-EPOXYSILANES WITH METALLATED ALKYLARYL SULPHONES. A NOVEL APPROACH TO ALLYLIC ALCOHOLS
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Lithiated alkylaryl sulphones (2a-c) react with α,β-epoxysilane (1) to yield O-trimethylsilyl allylic alcohols (3a-c), predominantly as Z isomers.The BF3-assisted reaction followed by treatment of the adduct with nBu4NF affords allylic alcohols.
- Masnyk, Marek,Wicha, Jerzy
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p. 2497 - 2500
(2007/10/02)
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- A NOVEL REACTION OF α-HALOEPOXIDES WITH TRIALKYLSTANNATES
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The reaction of α-haloepoxides with zinc powder or reagents containing tialkylstannate anion yields allylic alcohols by anti elimination of carbon halogen and adjacent carbon epoxy oxygen bonds.Appreciable Z -> E isomerization occurs in both types of reactions but the experimental results indicate that the conversion of erythro α-bromoepoxides to E allylic alcohols by zinc or trialkylstannates shows sufficient sterospecificity to be synthetically useful.
- Corey, L. D.,Singh, S. M.,Oehlschlager, A. C.
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p. 1821 - 1827
(2007/10/02)
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- MAGNESIUM-OPPENAUER OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES
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Using a magnesium-Oppenauer oxidation aldehydes and ketones are prepared from halomagnesium alkoxides, which in turn are the products of Grignard reactions.
- Byrne, Brian,Karras, Michael
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p. 769 - 772
(2007/10/02)
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- sp2-Hybridized β-Substituted Organo-lithium, -sodium, and -potassium Dianions; Preparation, Stability, and Reactivity
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The reaction of the substituted 2-chloroallyl alcohol (3a) with ethylmagnesium bromide followed by lithium was found to give the β-substituted organolithium derivative (4) of the type C=C().Intermediates of this type were also prepared directly from (E)-2-chlorocrotonaldehyde (2) or 2-chloroacrolein (19) by the same process using different Grignard reagents.The use of sodium or potassium as the metal in the second step of the process was found to give the corresponding organosodium or organopotassium derivative (24) or (25).A dilithiated dianion (26) was also obtained from the corresponding chlorohydrin (3d) by reaction with phenyl-lithium followed by lithium.These intermediates, which are stable species at room temperature, were found to react stereoselectively with electrophilic reagents leading to functionalized substituted allyl alcohols.The thermal stability of the lithiated dianion (4d) has also been investigated.
- Barluenga, Jose,Fernandez, Jose R.,Yus, Miguel
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p. 447 - 452
(2007/10/02)
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- STEREO- AND REGIOSELECTIVITY IN IODO DIOL FORMATION FROM ACYCLIC ALLYLIC ALCOHOLS
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Reaction of electrophiles with a variety of acyclic allylic alcohols was investigated.Both aqueous iodine and acetylhypoiodite convert certain alkenols into iodo diols and acetoxy iodo alcohols, respectively, with regio- and stereoselectivities as high as 99percent.Protection of alcohol group lowers the selectivity only slightly.Structural factors that control the regioselectivity of iodohydrin formation in these substrates have been delineated.Some of the iodo diols have been deiodinated, illustrating a simple two step procedure for converting allylic alcohols into threo-1,3-diols.
- Chamberlin, A. Richard,Mulholland, Robert L.
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p. 2297 - 2302
(2007/10/02)
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