51326-26-2Relevant articles and documents
Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides
Kotsuki, Hiyoshizo,Shimanouchi, Tomoyasu,Ohshima, Reiji,Fujiwara, Shunsuke
, p. 2709 - 2722 (1998)
The reaction of epoxides with lithium halides was efficiently promoted on the surface of silica gel in the absence of any solvent to give the corresponding β-halohydrins. The reactivity of lithium halides was shown to follow the order LiI > LiBr >> LiCl, and the reactivity of LiCl was dramatically increased by adding an equivalent amount of water to this system. On the other hand a similar reaction with α,β-epoxyketones produces the α-haloenone derivatives, presumably via halohydrin intermediates. The epoxide-opening reaction of (R)-(+)-styrene oxide was also investigated to clarify the stereochemical features of this reaction.
Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides: Access to Fully Substituted α-Amino Ketones
Velasco-Rubio, álvaro,Alexy, Eric J.,Yoritate, Makoto,Wright, Austin C.,Stoltz, Brian M.
supporting information, p. 8962 - 8965 (2019/11/14)
A versatile thermal Overman rearrangement of enantioenriched, cyclic allylic alcohols providing tertiary allylic amines has been developed. The vinyl bromide used to control enantioselectivity in a preceding CBS reduction is utilized as a synthetic handle
Synthetic Study toward the Total Synthesis of Taxezopidines A and B
Fan, Jian-Hong,Hu, Ya-Jian,Li, Chuang-Chuang,Li, Shaoping,Zhao, Jing
supporting information, p. 5905 - 5909 (2018/09/21)
A concise synthetic approach to construct the [6,8,6]-tricyclic core of taxezopidines A and B, which contains a synthetically challenging bridged bicyclo[5.3.1]undecane ring system bearing most of the desired functionalized groups and stereocenters, has b
Efficient Synthesis of Anastrephin via the Allylic Substitution for Quaternary Carbon Construction
Wada, Kyohei,Sakai, Masahiro,Kawashima, Hidehisa,Ogawa, Narihito,Kobayashi, Yuichi
supporting information, p. 1428 - 1432 (2016/05/24)
Lactone-moiety-attached 2-cyclohexylideneethyl picolinate was prepared through the OH-directed epoxidation (98% ds) of (R)-3-methylcyclohex-2-en-1-ol (99% ee), Horner-Wadsworth-Emmons olefination, conversion to the allylic moiety, and epoxide ring opening
Synthesis of 4,6-dimethyldibenzothiophene and 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene via Tilak annulation
Xu, Xiaoying,Li, Xiang,Wang, Anjie,Sun, Yinyong,Schweizer, W. Bernd,Prins, Roel
experimental part, p. 1754 - 1763 (2011/12/03)
1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4, 6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3- methylcyclohexanone was synthesized by conjugate addition of Me3Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex- 2-en-1-one by bromination-elimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF 3COOH. Copyright
Cyclic α-acylvinyl anionic synthons: A novel synthesis of 2-trimethylsilyl-3-methyl-cyclohexenone by the Wurtz-Fittig coupling reaction
Jyothi, Divya,HariPrasad
body text, p. 875 - 879 (2009/09/05)
2-Trimethylsilyl-3-methyl-cyclohexen-1-one: a cyclic α-acyl anionic synthon was prepared in good yield by the Wurtz-Fittig coupling reaction of 6-bromo-7-methyl-1,4-dioxaspiro[4,5]-6-decene with metallic sodium and chlorotrimethylsilane in anhydrous ether solvent. Copyright Taylor & Francis Group, LLC.
A remarkably simple one-step procedure for the preparation of α-bromo-α,β-unsaturated carbonyl compounds
Jyothi, Divya,Hariprasad
experimental part, p. 2309 - 2311 (2009/12/08)
An easy and convenient one-step procedure for the conversion of α,β-unsaturated carbonyl compounds into their corresponding bromo-enones using NBS-Et3N·3HBr in the presence of potassium carbonate in dichloromethane at 0°C to room temperature under very mild conditions in high yields and significantly shorter times, is reported. Georg Thieme Verlag Stuttgart.
Stereoselective solvent induced 1,3-proton transfer of an allylic alkoxide to a homoallylic alkoxide catalysed by a chiral lithium amide
Hansson, Maria,Arvidsson, Per I.,Nilsson Lill, Sten O.,Ahlberg, Per
, p. 763 - 767 (2007/10/03)
Stereoselective rearrangements of e.g. meso-epoxides by chiral lithium amides yield chiral allylic alcohols in high enantiomeric excess. Such products are useful synthetic intermediates. Lithium (S)-2-(pyrrolidin-1-ylmethyl)-pyrrolidide Li-2 has been foun
A novel and one step procedure for preparation of α-bromo-α,β-unsaturated carbonyl compounds
Ramanarayanan,Shukla, Vidyanand G.,Akamanchi
, p. 2059 - 2061 (2007/10/03)
A new one step method is developed for the preparation of α-bromo-α,β-unsaturated carbonyl compounds in moderate to good yields from corresponding α,β-unsaturated carbonyl compounds using DMP [1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(IH)-one] and te
A convenient and useful method of preparation of α-bromo enones from the corresponding enones using organic ammonium tribromide (OATB)
Bose, Gopal,Bujar Barua, Pankaj M.,Chaudhuri, Mihir K.,Kalita, Dipak,Khan, Abu T.
, p. 290 - 291 (2007/10/03)
Various acyclic α-bromo enones 2 as well as cyclic α-bromo enones 4 can be prepared from the corresponding acyclic enones 1 and cyclic enones 3 respectively, in a one-pot procedure by employing organic ammonium tribromide, such as cetyltrimethylammonium t
