Journal ArticleDOI
Enantioselective Synthesis of trans-4-Methylpipecolic Acid
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TLDR
An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described, based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring.Abstract:
An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).read more
Citations
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Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue.
Tsubasa Watanabe,Takamichi Imaizumi,Takumi Chinen,Yoko Nagumo,Masatoshi Shibuya,Takeo Usui,Naoki Kanoh,Yoshiharu Iwabuchi +7 more
TL;DR: The results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.
Journal ArticleDOI
Concise synthesis of alkaloid (-)-205B.
TL;DR: A short total synthesis of alkaloid (-)-205B by means of an anti-selective SN2' alkylation of an attractively functionalized cyclopropanol and diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation is described.
Journal ArticleDOI
Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation
Antoni Riera,Maria João Moreno +1 more
TL;DR: An overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented, showing their value as excellent precursors to cyclic compounds and the popularization of ring-closing metathesis has further increased their value.
Journal ArticleDOI
An efficient synthesis of nitrogen-containing heterocycles via a tandem carbenoid N―H insertion/ring-closing metathesis sequence
TL;DR: In this paper, a series of five-to eight-membered nitrogen-containing heterocycles were prepared via a general and efficient one-pot, two-component sequence featuring rhodium-catalyzed insertion of a vinyl-substituted α-diazocarbonyls into the N-H bond of the series of tert-butoxycarbonyl-(Boc)-protected amines, followed by ring-closing metathesis catalyzed by ruthenium benzylidene complexes.
Journal ArticleDOI
Asymmetric Synthesis of cis-4-and trans-3-Hydroxypipecolic Acids
TL;DR: In this article, an enantioselective synthesis of cis-4- and trans-3-hydroxypipecolic acids from 2,3-epoxy-5-hexen-1-ol is described.
References
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Journal ArticleDOI
Recent advances in olefin metathesis and its application in organic synthesis
Robert H. Grubbs,Sukbok Chang +1 more
TL;DR: In this paper, a review of recent advances in olefin metathesis focusing on the areas of ring-closing olefi cation (RCM) and cross-metathesis is presented.
Journal ArticleDOI
Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization
TL;DR: The use of 3A or 4A molecular sieves substantially increases the scope of the titanium(IV)-catalyzed asymmetric epoxidation of primary allylic alcohols as mentioned in this paper.
Journal ArticleDOI
Olefin Metathesis and Beyond
TL;DR: In this paper, the authors provide an overview of the development of catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups.
Journal ArticleDOI
Oxidation of α,β-un saturated aldehydes
TL;DR: A variety of methods for the conversion of α,β-unsaturated aldehydes to the corresponding acids have been explored as mentioned in this paper, and the best approach uses sodium chlorite and gives the desired transformation.
Journal ArticleDOI
Ring-Closing Metathesis and Related Processes in Organic Synthesis
TL;DR: The transition metal alkylidene-catalyzed olefin metathesis reaction and the related transition metal-mediated carbonyl olefination reaction are two such processes as discussed by the authors.
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