Umsetzungen von ungesättigten Organo-Stickstoffverbindungen mit Organoboranen bzw. Trichlorboran

Meller, A.; Gerger, W.

doi:10.1007/bf00912966

Cited by 16 publications

(2 citation statements)

References 6 publications

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“…At room temperature, these reactions proceeded slowly (Table 1, Entry 7) and heating at 110Ϫ130°C or high pressure were required. 1 H-and 13 C-NMR spectra of the raw products showed the presence of two isomers in each case (Table 1, Entries 4Ϫ8). The picrate of the major isomer (trans-3c) was isolated in its pure state by recrystallization (Et 2 O/MeOH) of a mixture of picrates (trans-3c/cis-3c ϭ 92:8), and its trans stereochemistry was established by X-ray analysis.…”

Section: Resultsmentioning

confidence: 99%

“…The NǞB coordination giving adduct 6 seems to be the first step of the reaction. Then, [1,3]-sigmatropic shift of the hydrogen atom (H) from N to C-3 proceeds to generate the imine complex 7. The CϭN bond formed undergoes allylboration through a six-membered transition state 8 immediately, the allyl group being added mainly (or quantitatively) in a trans fashion relatively to the substituent at C-3.…”

Section: Resultsmentioning

confidence: 99%

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Reductive 1,2-Allylboration of Indoles by Triallyl- and Triprenylborane − Synthesis of 2-Allylated Indolines

et al. 2000

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Reductive 1,2-Allylboration of Indoles by Triallyl- and Triprenylborane − Synthesis of 2-Allylated Indolines

et al. 2000

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With Other Boron Compounds

Whitfield¹

1988

Inorganic Reactions and Methods

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Heterocyclization and Spirocyclization Processes Based on Domino Reactions of N‐Tosylhydrazones and Boronic Acids Involving Intramolecular Allylborylations of Nitriles

Plaza

Parisotto

Valdés

2018

Chemistry A European J

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Polycyclic molecules featuring all-carbon quaternary bridgehead centers were synthesized through domino cyclizations between N-tosylhydrazones and boronic acids. Variations of the general cascade have been applied for the preparation of 3-quinuclidinones and related alkaloid-like scaffolds through transannular heterocyclizations. Moreover, the employment of 3-cyanopropyl and 4-cyanobutylboronic acids and α,β-unsaturated N-tosylhydrazones led to spirocycles through unprecedented formal [n+1] cyclizations, including the stereoselective spirocyclization of the Hajos-Parrish ketone. The common feature of all the new reactions described is the creation of an all-carbon quaternary center by formation of two Csp -C bonds on the hydrazonic carbon atom. DFT-based calculations suggested the occurrence of cascade processes, which involve a diazo compound carboborylation followed by a 1,3-borotropic rearrangement on an intermediate allylboronic acid and a novel bora-aza-ene cyclization.

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Umsetzungen von ungesättigten Organo-Stickstoffverbindungen mit Organoboranen bzw. Trichlorboran

Cited by 16 publications

References 6 publications

Reductive 1,2-Allylboration of Indoles by Triallyl- and Triprenylborane − Synthesis of 2-Allylated Indolines

Reductive 1,2-Allylboration of Indoles by Triallyl- and Triprenylborane − Synthesis of 2-Allylated Indolines

With Other Boron Compounds

Heterocyclization and Spirocyclization Processes Based on Domino Reactions of N‐Tosylhydrazones and Boronic Acids Involving Intramolecular Allylborylations of Nitriles

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