100350-03-6Relevant articles and documents
Highly enantioselective catalytic ketone allylation with Sn(CH2CH=CH2)4/RSn(CH2CH=CH 2)3 mixtures (R = Et, Bu)
Cunningham,Woodward
, p. 43 - 44 (2002)
In the presence of the monothiobinaphthol (MTB) ligand aryl ketones are allylated by mixtures of Sn(CH2CH=CH2)4/ RSn(CH2CH=CH2)3 (R = Et, Bu) in high e.e. The presence of water suppresses racemic back
Allylation of unactivated ketones by tetraallyltin accelerated by phenol. Application to asymmetric allylation using a tetraallyltin-BINOL system
Yasuda, Makoto,Kitahara, Noriko,Fujibayashi, Tatsuya,Baba, Akio
, p. 743 - 744 (1998)
The tetraallyltin-phenol system was mild and effective for allylation of unactivated ketones, giving tertiary alcohols in high yields. The asymmetric allylation was achieved by a tetraallyltin-homochiral BINOL (1,1'-bi-2-naphthol) system. The addition of
Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds
Fager, Diana C.,Lee, Kyunga,Hoveyda, Amir H.
, p. 16125 - 16138 (2019)
We disclose the results of an investigation designed to generate insight regarding the differences in the electronic and steric attributes of C-F, C-Cl, and C-Br bonds. Mechanistic insight has been gleaned by analysis of variations in enantioselectivity, regarding the ability of electrostatic contact between a halomethyl moiety and a catalyst's ammonium group as opposed to factors lowering steric repulsion and/or dipole minimization. In the process, catalytic and enantioselective methods have been developed for transforming a wide range of trihalomethyl (halogen = Cl or Br), dihalomethyl, or monohalomethyl (halogen = F, Cl, or Br) ketones to the corresponding tertiary homoallylic alcohols. By exploiting electrostatic attraction between a halomethyl moiety and the catalyst's ammonium moiety and steric factors, high enantioselectivity was attained in many instances. Reactions can be performed with 0.5-5.0 mol % of an in situ generated boryl-ammonium catalyst, affording products in 42-99% yield and up to >99:1 enantiomeric ratio. Not only are there no existing protocols for accessing the great majority of the resulting products enantioselectively but also in some cases there are hardly any instances of a catalytic enantioselective addition of a carbon-based nucleophile (e.g., one enzyme-catalyzed aldol addition involving trichloromethyl ketones, and none with dichloromethyl, tribromomethyl, or dibromomethyl ketones). The approach is scalable and offers an expeditious route to the enantioselective synthesis of versatile and otherwise difficult to access aldehydes that bear an α-halo-substituted quaternary carbon stereogenic center as well as an assortment of 2,2-disubstituted epoxides that contain an easily modifiable alkene. Tertiary homoallylic alcohols containing a triazole and a halomethyl moiety, structural units relevant to drug development, may also be accessed efficiently with exceptional enantioselectivity.
Asymmetric allyltributylstannane addition to ketones catalyzed by chiral PYBOX-In(III) complex immobilized in ionic liquid
Lu, Jun,Ji, Shun-Jun,Teo, Yong-Chua,Loh, Teck-Peng
, p. 7435 - 7437 (2005)
An indium complex of chiral PYBOX was applied in the catalytic asymmetric allylation of ketones in the ionic liquid. It was found that this chiral indium complex was strong enough to promote the reaction of ketones with allyltributylstannane smoothly. The
Enantioselective allylation of ketones catalyzed by N,N′-dioxide and indium(III) complex
Zhang, Xin,Chen, Donghui,Liu, Xiaohua,Feng, Xiaoming
, p. 5227 - 5233 (2007)
(Chemical Equation Presented) Complexes of (S)-pipecolic acid-, L-proline-, and other amino acid-derived N,N′-dioxides coordinated with different metal ions have been investigated in the enantioselective allylation of ketones. A variety of aromatic ketone
Catalytic enantioselective allylation of ketones via a chiral indium(III) complex
Teo, Yong-Chua,Goh, Joshua-Daniel,Loh, Teck-Peng
, p. 2743 - 2745 (2005)
(Chemical Equation Presented) A chiral indium complex has been discovered to effect high enantioselectivities in the addition of allyltributylstannanes to ketones. The allylation of a variety of aromatic, α,β-unsaturated and aliphatic ketones resulted in
Enantioselective catalytic allylation of arylmethylketones using tetraallyltin and tin(IV) chloride mixtures
Prieto, Oscar,Woodward, Simon
, p. 1515 - 1519 (2006)
Reaction of SnCl4 with Sn(CH2CHCH2) 4 in the presence of water and monothiobinaphthol [2,2′-C 20H12(OH)(SH)] allows the formation of a selective catalyst for the allylation of ketones (up t
Enantioselective allylation of ketones catalyzed by chiral In(III)-PYBOX complexes
Lu, Jun,Hong, Mei-Ling,Ji, Shun-Jun,Teo, Yong-Chua,Loh, Teck-Peng
, p. 4217 - 4218 (2005)
In the presence of 20 mol% of chiral catalytic complex prepared from In(OTf)3 and chiral PYBOX, allyltributylstannane reacted with achiral ketones to afford the corresponding homoallylic alcohols in moderate to high enantioselectivities (54-95%
Spiro-dihydrobenzo-silole diphenol compounds, synthesis method and application thereof (by machine translation)
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Paragraph 0702-0712, (2020/06/17)
The invention discloses a spirodiclole diphenol compound as shown in a formula I as well as a synthesis method and application thereof. The method has the characteristics of simplicity and convenience in operation, easily available raw materials, mild rea
