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[(tert-Butyldimethylsilyl)oxy]methanethiol and [(tert-Butyldiphenylsilyl)oxy]- methanethiol—Nucleophilic Protected H2S Equivalents
Download2015-01-01
Dong, Shuai, Clive, Derrick L. J., Gao, Jin-Ming
[(tert-Butyldimethylsilyl)oxy]methanethiol [HSCH2OSiMe2Bu-t] is a nucleophilic reagent for 2 introduction of a protected bivalent sulfur; this reagent is complementary to the electrophilic reagent p-MeC6H4SO2SCH2OSiMe2Bu-t. The thiol is prepared by the action of HSLi on...
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2015-01-01
Shao, Wenjie, Clive, Derrick L. J.
A new family of routes to substituted phenols has been developed. 2-Bromo-3- methoxycyclohex-2-en-1-ones are readily deprotonated at C-6 and the resulting anions react smoothly with a variety of electrophiles; treatment with DBU in PhMe at room temperature then results in efficient aromatization...
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Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones - Assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit.
Download2016-01-01
Yu, Goujun, Clive, Derrick L. J.
Conjugate addition of Me3SiMe2SiLi to cycloalk-2-en-1-ones, ketalization, Tamao-Fleming oxidation (Bu4NF, then H2O2, KHCO3), TPAP oxidation and acid hydrolysis generates 2-methyl cycloalkane-1,3-diones. Ketalization is needed in order to prevent addition of Me3Si- to the carbonyl. The...
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2021-01-01
Szymor-Pietrzak, Damian, Khan, Muhammad N., Pagès, Anaïs, Kumar, Ajay, Depner, Noah, Clive, Derrick L. J.
meta-Aminophenols are formed by the action of DBU on 3-amino-2-chlorocyclohex-2-en-1-ones at room temperature in MeCN. The chloro compounds are generated by treating 3- aminocyclohex-2-en-1-ones with the easily prepared halogenating agent BnNMe3.ICl2 in MeOHCH2Cl2. The amino group must carry two...
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2019-01-01
Palanivel, Ashokkumar, Mubeen, Sidra, Warner, Thomas, Ahmed, Nayeem, Clive, Derrick L. J.
Enol ethers are formed by radical decarboxylation of -alkoxy -phenylthio acids via the corresponding Barton esters. The phenylthio acids were usually made by the known regioselective reaction of ,-epoxy acids with PhSH in the presence of InCl3, followed by Oalkylation of the resulting...
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Formation of meta-Arylsulfanyl- and meta-(Alkylsulfanyl)phenols from Cyclohexane-1,3-diones
Download2018-01-01
Thanh, Nhan Do Van, Patra, Subrata, Clive, Derrick L. J.
Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or (alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at...
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Formation of meta-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones.
Download2016-01-01
Yu, Guojun, Clive, Derrick L. J.
Addition of Grignard- or other organometallic reagents to 3-halocyclohex-2-en- 1-ones bearing an alkyl or aryl group at C-5, followed by mild acid treatment and exposure to DBU at room temperature, generates meta-substituted phenols in which the newly introduced meta substituent originates from...
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2015-01-01
Chea, JongMyong, Clive, Derrick L. J.
N-Boc (S)-proline was converted into (2S)-2-[(phenylselanyl)methyl]pyrrolidine which was alkylated on nitrogen with 2-bromo-1-(4-methoxyphenyl)ethan-1-one. Reaction with vinyllithium, 6-exo-trigonal radical cyclization (Bu3SnH, AIBN, PhMe, 110 °C), dehydration (P2O5, H3PO4) and demethylation...
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2016-01-01
Dong, Shuai, Indukuri, Kiran, Clive, Derrick L. J., Gao, Jin-Ming
Piperazinedione 13, representing the BC ring system of the anti-prostate cancer fungal metabolite MPC1001 was prepared by a route in which a sulfur-stabilized carbanion derived from 22 cyclizes onto the terminal ester of the chain attached to N1. Another model, 14, was synthesized by cyclization...
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2019-01-01
Hattori, Hiroyuki, Mitsunga, Tohru, Clive, Derrick L. J.
Two vanilloids, (5E)-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one (1) and 4-[3-hydroxydecyl]-2-methoxyphenol (2), isolated from the dried seeds of Grains of Paradise (Aframomum melegueta), were synthesized; the latter compound was made as the S-enantiomer and the material derived from the seeds...