June 2024
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22 Reads
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1 Citation
Organic Letters
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Publications (3)
November 2010
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27 Reads
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70 Citations
Organic Letters
A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.
February 2009
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24 Reads
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92 Citations
Organic Letters
Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.
Citations (3)
... could possibly generate the isoimide intermediate 25 . Thereafter, the addition of a chiral N-heterocyclic carbene (NHC) [26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] to the isoimide could generate the acylazolium intermediate, which make the carbonyl carbon electrophilic enough for the atroposelective amidation of less nucleophilic N-aryl acid amides (Fig. 1B) [42][43][44][45] . Based on this concept, herein, we report the organocatalytic atroposelective synthesis of Naryl phthalimides via the traditional N-C C=O disconnection under mild conditions [46][47][48] . ...
- Citing Article
June 2024
Organic Letters
... 10 2, 198.3, 144.1, 135.7, 129.9, 127.4, 85.4, 76.7, 56.2, 48.8, 21.5 11 To a solution of allenol 1a (17 mmol, 1 equiv) in water-saturated CH 2 Cl 2 (60 mL) at 0 ᵒC, Dess-Martin-Periodinane ( 34 mmol, 2 equiv) was added, and the mixture was allowed to warm to room temperature. Meanwhile after 15 minutes, in each 5 minutes, 6 mL of water-saturated CH 2 Cl 2 was added to the reaction mixture until the TLC shows complete consumption of the starting material. ...
- Citing Article
November 2010
Organic Letters
... Zn/ EtOH [13] mediated reductive ring opening of iodo-intermediate 15 furnished the hydroxy olefin 16 in 96 % yield. Epoxidation of 16 with m-CPBA in dichloromethane followed by treatment with a catalytic amount of CSA [14] provided the cis-and trans -THP compounds 17 a and 17 b in 7 : 3 ratio in 90 % yield. In order to establish the stereochemistry at the newly generated stereocenter at C-16, 17 a and 17 b were subjected to hydrogenation to produce 18 and 13. ...
- Citing Article
February 2009
Organic Letters