The stereoselective addition of titanium(IV) enolates of 1,3-oxazolidin-2-one and 1,3-thiazolidine-2-thione to cyclic N-acyliminium ion. The total synthesis of (+)-isoretronecanol |
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| Authors: | Elaine Pereira Maria Alice Böckelmann |
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| Institution: | a Instituto de Química, UNICAMP, PO Box 6154, 13084-971, Campinas, SP, Brazil
b Universidade Estadual do Oeste do Paraná, PO Box 85903-000, Toledo, PR, Brazil |
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| Abstract: | (+)-Isoretronecanol (1) has been prepared in four steps and 36% overall yield via the diastereoselective addition of the titanium(IV) enolate derived from N-4-chlorobutyryl-1,3-thiazolidine-2-thione (3) to N-Boc-2-methoxypyrrolidine (5), which afforded 2-substituted pyrrolidine 7 in 84% yield (8:1 diastereoisomeric ratio), followed by reductive recovery of the chiral auxiliary and cyclization. |
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| Keywords: | Titanium(IV) enolates 1 3-Oxazolidin-2-one 1 3-Thiazolidine-2-thione N-Acyliminium ion (+)-Isoretronecanol |
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