Synthesis of 8,8 '-disubstituted 1,1 '-binaphthyls stable to atropisomerization: 2,2 '-dimethyl-1,1 '-binaphthalene-8,8 '-diol and 2,2 '-dimethyl-8,8'-bis(4-tert-butyloxazolyl)-1,1 '-binaphthyl

Authors
Kolotuchin, SV Meyers, AI
Citation
Sv. Kolotuchin et Ai. Meyers, Synthesis of 8,8 '-disubstituted 1,1 '-binaphthyls stable to atropisomerization: 2,2 '-dimethyl-1,1 '-binaphthalene-8,8 '-diol and 2,2 '-dimethyl-8,8'-bis(4-tert-butyloxazolyl)-1,1 '-binaphthyl, J ORG CHEM, 64(21), 1999, pp. 7921-7928
Citations number
64
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
21
Year of publication
1999
Pages
7921 - 7928
Database
ISI
SICI code
0022-3263(19991015)64:21<7921:SO8'1'>2.0.ZU;2-S
Abstract
Axially chiral binaphthyls 3a and 3b were synthesized taking, advantage of Ullman coupling of 4a and 4b, respectively. The binaphthyls were shown to b e stable to atropisomerization. Binaphthol 3b was resolved with (-)-(1S)-me nthyl chloroformate (11). R-axis diastereomer of bisoxazoline 3b was used f or enantioselective cyclopropanation of styrene with ethyl diazoacetate.