Title of article
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
Author/Authors
Pereira، نويسنده , , Elaine and Fلtima Alves، نويسنده , , Conceiçمo de and Bِckelmann، نويسنده , , Maria Alice and Pilli، نويسنده , , Ronaldo A.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2005
Pages
3
From page
2691
To page
2693
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.
Keywords
1 , (+)-Isoretronecanol , N-acyliminium ion , 3-Thiazolidine-2-thione , Titanium(IV) enolates , 1 , 3-Oxazolidin-2-one
Journal title
Tetrahedron Letters
Serial Year
2005
Journal title
Tetrahedron Letters
Record number
1845377
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