Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide

Authors
McNulty, J Grunner, V Mao, J
Citation
J. Mcnulty et al., Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide, TETRAHEDR L, 42(33), 2001, pp. 5609-5612
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
33
Year of publication
2001
Pages
5609 - 5612
Database
ISI
SICI code
0040-4039(20010813)42:33<5609:SAOGRT>2.0.ZU;2-N
Abstract
Controlled addition of Grignard reagents to tartaric acid derived bis-Weinr eb amide 3 provides a facile, direct entry to desymmetrized 1,4-functionali zed-syn-2.3-diol intermediates 4 and to C-2-symmetrical 1,4-diketones 5. Th e synthetic versatility of this method is exemplified by short syntheses of the natural plant growth regulator 10 and the synthetically valuable cyclo octene derivative 13. (C) 2001 Elsevier Science Ltd. All rights reserved.