✦ LIBER ✦

Stereoselective synthesis of 1,4-dideoxy-1,4-imino-d-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline

✍ Scribed by A Madhan; B Venkateswara Rao

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 123 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01366-2

No coin nor oath required. For personal study only.

✦ Synopsis

A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation.

📜 SIMILAR VOLUMES

Synthesis of 2R,3S,4R-dihydroxyproline f

Synthesis of 2R,3S,4R-dihydroxyproline from D-ribonolactone

✍ J.C. Dho; G.W.J. Fleet; J.M. Peach; K. Prout; P.W. Smith 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 140 KB

ChemInform Abstract: Stereoselective Syn

ChemInform Abstract: Stereoselective Synthesis of 1,4-Dideoxy-1,4-imino-L-lyxitol and 1,5-Dideoxy-1,5-imino-D-ribitol.

✍ Ki Chang Jang; Ill-Yun Jeong; Min Suk Yang; Sang Uk Choi; Ki Hun Park 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Stereoselective synthesis of (2S,3S,4R,5

Stereoselective synthesis of (2S,3S,4R,5S)-proline-3,4,5-d3

✍ Makoto Oba; Tsutomu Terauchi; Jun Hashimoto; Tomohiro Tanaka; Kozaburo Nishiyama 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 227 KB

A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCI2(PPh3) 3 followed by RuO~-oxidation gave a 3,4-dideuterated L-pyroglutamic acid derivative which is considered to be a promising precursor for various deuterated amino acids. The present study demonstrates a stereoselective reduct

Stereoselective synthesis of (1′S,3R,4R)

Stereoselective synthesis of (1′S,3R,4R)-4-acetoxy-3-(2′-fluoro-1′-trimethylsilyloxyethyl)-2-azetidinone

✍ Ivan Plantan; Michel Stephan; Uroš Urleb; Barbara Mohar 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 218 KB

A stereoselective synthesis of (1 0 S,3R,4R)-4-acetoxy-3-(2 0 -fluoro-1 0 -trimethylsilyloxyethyl)-2-azetidinone as a new fluorine-containing intermediate towards b-lactams, is described. The synthetic key step relies upon the dynamic kinetic resolution (DKR) of ethyl 2-benzamidomethyl-4-fluoro-3-ox

Ring-Closing Metathesis of Chiral Allyla

Ring-Closing Metathesis of Chiral Allylamines. Enantioselective Synthesis of (2S,3R,4S)-3,4-Dihydroxyproline.

✍ Ruben Martin; Montserrat Alcon; Miquel A. Pericas; Antoni Riera 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 261 KB 👁 1 views

ChemInform Abstract: Chirospecific Synth

ChemInform Abstract: Chirospecific Synthesis of 1,4-Dideoxy-1,4-imino-D-arabinitol and 1,4-Dideoxy-1,4-imino-L-xylitol via One-Pot Cyclization.

✍ J. H. KIM; M. S. YANG; W. S. LEE; K. H. PARK 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

The protected compounds (V) and (IX) are treated with iodine in MeOH to give pyrrolidines (VI) and (X), respectively. Iodine is found to be an efficient catalyst for deprotection of several O-and N-protecting groups. -(KIM, J.