The N -Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction. European Journal of Organic Chemistry 2016 , 2016 (15) , 2647-2652.
discovered an unprecedented method for carbon-carbon bond forming reaction using tertiary aldehyde as a traceless activation group and identified a new pathway for the generation of tertiary Aug 06, 2014 · Over the past four decades, significant advances have been made in the development of traceless activation groups (TAGs) such as cuprates, boronic acids, halides, and Grignard reagents that enable a broad range of organic structures to participate as nucleophiles or donor components in this 1,4-coupling pathway. 2,3 Expanding upon this theme, we recently questioned whether simple and abundant carboxylic acids might be generically 5 employed as a traceless activation group for radical 1,4 Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin. Journal of the American Chemical Society. 136: 10886-9. PMID 25032785 DOI: 10.1021/ja505964r : 1: 2014: Noble A, MacMillan DW. Photoredox α-vinylation of α-amino acids and N-aryl amines. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin. Journal of the American Chemical Society. 136: 10886-9. PMID 25032785 DOI: 10.1021/ja505964r : 1: 2014: Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW. Dual catalysis. We attempted another N-protective group, benzyloxycarbonyl (Cbz), and N-Cbz-Pro-OPht exhibited similar reactivity to N-Boc-Pro-OPht (see 3r and 3s). Unfortunately, active esters of three natural amino acids including cysteine, histidine and arginine gave some by-products because of side reaction on side chains of the amino acids under the
Jun 01, 2004 · Designing a new anchoring group can be essential for synthesis success, especially for small molecules on solid supports. Many novel linkers have recently been developed. Traceless linkers can be excised efficiently and quantitatively when desired while leaving behind no trace of the solid-phase synthesis.
a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photo-redox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, α-oxy, and α-amino acids, provides a versatile CO 2-extrusion platform to generate Michael donors without the require- Mar 27, 2015 · The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two‐step process, thereby providing a highly effective approach to 5‐unsubstituted pyrrolidines. Chu L; Ohta C; Zuo Z; MacMillan DWC Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin. J. Am. Chem. Soc. 136, 10886–10889 (2014). [PMC free article] [Google Scholar] Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin L. Chu, C. Ohta, Z. Zuo, D. W. C. MacMillan Science, 345, 437-440
Aug 06, 2014 · Over the past four decades, significant advances have been made in the development of traceless activation groups (TAGs) such as cuprates, boronic acids, halides, and Grignard reagents that enable a broad range of organic structures to participate as nucleophiles or donor components in this 1,4-coupling pathway. 2,3 Expanding upon this theme, we recently questioned whether simple and abundant carboxylic acids might be generically 5 employed as a traceless activation group for radical 1,4
We attempted another N-protective group, benzyloxycarbonyl (Cbz), and N-Cbz-Pro-OPht exhibited similar reactivity to N-Boc-Pro-OPht (see 3r and 3s). Unfortunately, active esters of three natural amino acids including cysteine, histidine and arginine gave some by-products because of side reaction on side chains of the amino acids under the Sulfonyl as a Traceless Activation Group for Enantioselective Mannich Reaction Catalyzed by Thiourea to Access Chiral β-Aminophosphonates Yungui Peng* Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. of China Email: pengyungui@hotmail.com Mar 09, 2020 · We reasoned appending a vinyl group to the carbene C., Zuo, Z. & MacMillan, D. W. C. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Dec 18, 2014 · Chu L, Ohta C, Zuo Z, MacMillan DWC. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin. J. Am. Chem. Soc. 2014; 136:10886–10889. [PMC free article]