Stereodivergent and regioselective synthesis of 3,4-cis- and 3,4-trans-pyrrolidinediols from alpha-amino acids.
[reaction: see text] Highly stereodivergent Woodward-Prevost reaction applied to iodoacetates derived from homochiral alpha-amino acids afforded enantiopure 3,4-cis- and 3,4-trans-pyrrolidinediol derivatives, with control over the protecting group, allowing for differential protection.
Kim
Jin Hyo
JH
Division of Applied Life Science, BK21 program, Department of Agricultural Chemistry, Gyeongsang National University, Jinju 660-701, South Korea.
Long
Marcus J C
MJ
Kim
Jun Young
JY
Park
Ki Hun
KH
D000085:Acetates / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D007461:Iodoacetates / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
C500185:3,4-pyrrolidinediol; D000085:Acetates; D000498:Allyl Compounds; D000596:Amino Acids; D007461:Iodoacetates; D011759:Pyrrolidines; C498551:allyl acetate