First enantioselective non-biological synthesis of asymmetrised tris(hydroxymethyl)methane (THYM*) and bis(hydroxymethyl)acetaldehyde (BHYMA*)

Authors
Izzo, I Scioscia, M Del Gaudio, P De Riccardis, F
Citation
I. Izzo et al., First enantioselective non-biological synthesis of asymmetrised tris(hydroxymethyl)methane (THYM*) and bis(hydroxymethyl)acetaldehyde (BHYMA*), TETRAHEDR L, 42(32), 2001, pp. 5421-5424
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
32
Year of publication
2001
Pages
5421 - 5424
Database
ISI
SICI code
0040-4039(20010806)42:32<5421:FENSOA>2.0.ZU;2-B
Abstract
An asymmetric synthesis of a chiral non-racemic (O-benzyl, O'-silyl) deriva tive of the latent C-3,-symmetric tris(hydroxymethyl)methane (THYM*) and of the bis(hydroxymethyl)acetaldehyde (BHYMA*) in 6 steps, 38% overall yield and 7 steps, 36% overall yield, respectively, is described starting from th e commercially available 4-nitrobanzoate derivative of 17. The method invol ves the Sharpless asymmetric epoxidation and a regioselective copper-mediat ed oxirane ring opening, as key steps. (C) 2001 Elsevier Science Ltd. All r ights reserved.