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Chelation Control in the Ring Opening and Organometallic Addition of α,β‐Epoxy Aldehydes: a New Entry to Amino Dihydroxyethylene Dipeptide Isostere Subunits
Author(s) -
Righi Giuliana,
Chionne Andrea,
Bonini Carlo
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:18<3127::aid-ejoc3127>3.0.co;2-3
Subject(s) - chemistry , isostere , dipeptide , enantioselective synthesis , diol , chelation , ring (chemistry) , yield (engineering) , epoxy , stereochemistry , amino acid , organic chemistry , catalysis , biochemistry , materials science , metallurgy
Selective ring opening and subsequent organometallic addition to α,β‐epoxy aldehydes is found to afford anti ‐ syn 3‐bromo‐1,2‐diols in high stereo and chemical yield. This sequence is utilized for the enantioselective synthesis of (2 S ,3 R ,4 R )‐2‐amino‐1‐cyclohexyl‐6‐methylheptane‐3,4‐diol (an isomer of the Abbott amino diol).