174787-77-0

Upstream product

• 174787-76-9 (4R,5R)-5-allyl-3-tert-butoxycarbonyl-4-methyl-2-oxazolidinone 
• 82353-56-8 (2R)-2-N-t-butoxycarbonyl-aminopropanal 
• 762-72-1 allyl-trimethyl-silane 
• 115269-78-8 (4R,5R)-5-allyl-4-methoxy-2-oxazolidinone 
• 174851-37-7 (4R,5R)-5-allyl-4-methyl-2-oxazolidinone 

Relevant academic research and scientific papers

Chiral allylsilane additions to chiral N-Boc-a-amino aldehydes

Addition of chiral allylsilane 4 to chiral W-Boc-α-amino aldehydes in the presence of SnCl2 in CH2Cl2 at -78 °C affords 1,2-syn homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The diastereoselectivity depends on the aldehyde absolute configuration, with (R)-α-aminoaldehydes (matched case/anti-Felkin addition) exhibiting higher stereoselectivity than its enantiomer (mismatched case/Felkin addition). Thieme Stuttgart.

Synthetic application of chiral 4-methoxy-2-oxazolidinone synthons to 2-amino alcohols of biological interest

The versatility as chiral synthons of (4S, 5S)- and (4R, 5R)-5-allyl-4-methoxy-2-oxazolidinones, readily obtainable from 3-[(1S)-2-exo-alkoxy-1-apocamphanecarbonyl]-2-oxazolone, is demonstrated by the facile stereospecific conversions to (2R, 3S)-3-amino-2-hydroxy-3-phenylpentanoic acid, (2R, 3R, 5E, 7E)-2-amino-5,7-tetradecadien-3-ol and (2S, 3R)-dihydrosphingosine.