Expedient synthesis of β,β-disubstituted α-methylenepropionates

On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

“…Yield 54%; spectroscopic data for this compound are inagreement with those reported in literature [28]. The ester prepared above (50 mmol) in toluene (150 mL) under stirring at −10 • C in a N 2 atmosphere was treated dropwise with a 25% DIBAH solution in toluene (120 mmol).…”

Nickel-catalysed asymmetric SN2′ substitution chemistry of Baylis–Hillman derived allylic electrophiles

“…We selected the conversion of the allylic chloride (1a) and acetate (1b) as representative non-symmetrical allylic electrophiles for two reasons: firstly, these species are readily attained through simple Baylise Hillman chemistry [7], and secondly, a reliable chiral GC assay for the conversion yield and ee determination of product 2 was already available [8] (Scheme 3). The ether 1c was selected to allow direct comparison with the work of Nobuyoshi and RajanBabu [3a].…”

“…BINAP and Josiphos were commercial samples. Compounds 1a and 1b were prepared according to literature procedures [7,10]. A solution of sulfoxide precursor (0.45 g, 1.05 mmol) in THF (10 mL) was cooled to À78 C under argon.…”

γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides

“…25 In the current study, the scope of allylic bromides is increased (Scheme 2). Substrates bearing a nitrile group (3g) and alkyl keto group (3h) reacted with excellent regioselectivity (γ/α > 49:1).…”