“…L-glyceraldehyde acetal was converted into alkene 1 in 85% yield through a Wittig reaction according to a method described in a previous study. 5 Alkene 1 was then converted into compound 2 in 96% yield with Pd/C catalyst via a standard hydrogenation. Compound 3 was prepared by the reaction of 2 with (R)tert-butylsulfinamide in the presence of anhydrous CuSO 4 .…”
Section: Scheme 2 Retrosynthesis Of L-hydroxypipecolic Acidmentioning
A new synthetic approach toward l-hydroxypipecolic acid is described. This reaction sequence involves eight steps overall, starting from commercially available and inexpensive l-glyceraldehyde acetal. The strategy makes use of readily available reagents and can be used as a preparative synthesis of l-hydroxypipecolic acid. Most of the reaction steps proceed with moderate-to-good yields and do not require any unusual or expensive reagents.
“…L-glyceraldehyde acetal was converted into alkene 1 in 85% yield through a Wittig reaction according to a method described in a previous study. 5 Alkene 1 was then converted into compound 2 in 96% yield with Pd/C catalyst via a standard hydrogenation. Compound 3 was prepared by the reaction of 2 with (R)tert-butylsulfinamide in the presence of anhydrous CuSO 4 .…”
Section: Scheme 2 Retrosynthesis Of L-hydroxypipecolic Acidmentioning
A new synthetic approach toward l-hydroxypipecolic acid is described. This reaction sequence involves eight steps overall, starting from commercially available and inexpensive l-glyceraldehyde acetal. The strategy makes use of readily available reagents and can be used as a preparative synthesis of l-hydroxypipecolic acid. Most of the reaction steps proceed with moderate-to-good yields and do not require any unusual or expensive reagents.
“…Addition of isopropylmagnesium chloride to crotonaldehyde followed by kinetic resolution provided a single enantiomer of 18 (Scheme 5). [26][27][28] Esterification with methacryloyl chloride provided R,β-unsaturated allylic ester 4 in 70% yield and >99% ee.…”
mentioning
confidence: 99%
“…The initial stereocenter of ester 4 was established with complete enantioselectivity. Addition of isopropylmagnesium chloride to crotonaldehyde followed by kinetic resolution provided a single enantiomer of 18 (Scheme ). − Esterification with methacryloyl chloride provided α,β-unsaturated allylic ester 4 in 70% yield and >99% ee. 5 Chiral Induction and Chirality Transfer…”
Chiral quaternary carbon stereocenters can be established with high diastereoselectivity by a silylene transfer/Ireland-Claisen rearrangement. The utility of this method was demonstrated by application to a synthesis of (+)-5-epi-acetomycin. [reaction: see text]
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