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A pedagogical technique, named the Bridge activity, has been developed to assist students' transition from preclass preparation to in-class learning within a flipped organic chemistry course. Bridge activities form the basis of an initial interactive discussion to activate students' prior knowledge and encourage meaningful learning. This paper describes the rationale and theoretical basis for this technique, provides examples, offers solutions to large-class logistical considerations, and presents results from an analysis of student participation and perceptions of usefulness as reported in a questionnaire.

Demands are placed on undergraduate courses in chemistry to develop transferable skills, such as teamwork, alongside subject content and technical skills. Such skills can be developed by implementing pedagogies which involve students working together. Such pedagogies can, however, pose various challenges, including unfavourable student perceptions and experiences including the occurrence of dysfunctional student teams. This article presents a research-informed group project assignment delivered as part of an upper-year undergraduate chemistry course which has been found to overcome these challenges. The instructional activity is characterized by a high degree of structure and support for teamwork. Student perceptions, collected by survey and interview, and peer- and self-evaluations of contributions to the work of the groups reveal that students have experienced the activity positively. Many perceived disadvantages of working in a team to complete a project were either reportedly not experienced or could be overcome by the students, while perceived advantages were often reported to be experienced. Dysfunction within teams did not represent a significant issue.

The effectiveness of pyrrole formation using popular metal catalysts such as AgOTf or 'cationic' gold(I) complexes was examined. Either silver or gold catalysts efficiently facilitate the reactions between imines and alkynes in forming functionalized pyrroles in good yields.

The synthesis of derivatives of nitiol containing a hydroxyl function at the 1-position was completed in the laboratory. Important synthetic operations within the sequence forming the A-ring of nitiol included a siloxy-expoxide rearrangement reaction, a diastereoselective Pausopn-Khand reaction, and a Norrish type 1 photofragmentation.

The construction of 1-azaspirocyclic cycloalkanones using a siloxy-epoxide semipinacol ring expansion process is examined. The formation of functionalized 6-azaspiro[5,4]-decan-1-ones (1-azaspirocyclic cyclopentanones) proceeded in high chemical yield with little diastereoselectivity.

A study is conducted to demonstrate that substrates of general structure 2-(1-hydroxycyclobutyl)-p-toluenesulfonylenamides can be induced to undergo ring expansion reactions to form highly fictionalized 1-azaspirocyclopentanones. Reactions promoted by N-bromosuccinimide tend to proceed in higher yields (80-95%) and with greater diastereoselectivity (3:1-1:0) compared to those reactions promoted by a Bronsted acid.

Enol trifluoromethanesulfonates (triflates) derived from N-protected lactams undergo nickel(II)-chloride- and chromium(II)-chloride-promoted carbonyl additions to aldehydes. The yields of this process range from 42%-84%. Key words: nickel(II) chloride, chromium(II) chloride, carbonyl addition, lactam-derived enol triflate.

Successful efforts for the first stereoselective total synthesis of quinine are described.

The key compound responsible for the aroma of bread, 6-acetyl-1,2,3,4-tetrahydropyridine, was constructed in an efficient three-step procedure from 2-piperidone in an overall yield of 56%. This compound was liberated in the final step under basic condition and a related synthetic route produced 2-acetyl-1-pyrroline, the principal component of cooked rice, in 10% overall yield.

The reaction between electron-deficient acyclic enamine derivatives and electron-rich 1-arylalkynes was carried out by using cationic gold(I) species as catalysts in an intramolecular process to generate annulated 1-amido-substituted indene derivatives as the major products. The reaction gives yields in the range between 21% and 98% and in certain cases a two-step process that includes a subsequent alkene isomerization gave better yields.

The formation of nitrogen-containing polycyclic structures via a platinum(ii)-catalyzed addition/Friedel-Crafts ring closure of the various enesulfonamides and enamides is discussed. Regioselectivity observed in the addition of nucleophile to the complex is shown to be the most important mechanism of the reaction.

The development of a synthetic method to the A-B ring system within the fusicoccane family of diterpenes is described. Key steps in the synthesis included a diastereoselective Pauson-Khand reaction, a Norrish 1 photofragmentation, a Charette cyclopropanation, and a ring-closing metathesis process.

A study was conducted to analyze the synthetic route incorporating an N-bromosuccinimide (NBS)-promoted semipinacol rearrangement to the 6-azaspiro[4.5]decane fragment within halichlorine. The newly developed reaction has the capability to produce azaspirocyclic ketone products in a highly selective manner.

The conversion of sterically hindered carboxylic acids to N-methoxy-N-methyl amides can be efficiently carried out with 1.1 equiv of methanesulfonyl chloride, 3 equiv of triethylamine, and 1.1 equiv of N-methoxy-N-methylamine. N-methoxy-N-methylmethanesulfonamide, the major byproduct for these reactions, can be removed by placing the product mixture under vacuum for 14-24 hours.

A novel method of promoting phosphine-catalyzed gamma-addition reaction was developed through the use of nitrogen pronucleophiles. The design featured the novel reactivity of phosphine to induce addition of carbon and oxygen pronucleophiles to the 4-position of alkynoates. It was shown that phosphines were able to mediate the addition reaction by acting as a nucleophilic trigger.

Dehydroamino acids act as precursors to saturated amino acids, and a new an unprecedented reactivity pattern for alkynoates-nucleophilic addition at the alpha-position has been suggested.It is assumed that the high nucleophilicity of the phosphine relative to acid-base reactions account for the ability to redirect the regioselectivity of adding a nucleophile from the classical beta-addition mode to an alpha addition.