Premium
Synthesis and chiroptical properties of a novel C 2 ‐symmetric binaphthyl phosphortriamide (”chiral HMPA“)
Author(s) -
Meyers A. I.,
Nguyen Thanh,
Stoianova Diana,
Sreerama N.,
Woody Robert W.,
Koslowski Axel,
Fleischhauer Jörg
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:5/6<431::aid-chir6>3.0.co;2-8
Subject(s) - chemistry , cndo/2 , chirality (physics) , axial chirality , azepine , cotton effect , stereochemistry , computational chemistry , circular dichroism , enantioselective synthesis , organic chemistry , molecule , catalysis , chiral anomaly , physics , fermion , quantum mechanics , nambu–jona lasinio model
By use of an asymmetric Ullmann coupling involving chiral naphthalene oxazolines 1 , the title compounds were prepared in good yields and with high diastereoselectivity. Hydrolysis of the binaphthyl oxazolines 2 led to the di‐aldehydes 5 , which were transformed into the azepine derivative, 6. The latter was treated with the appropriate phosphoryl halide to access the chiral HMPA systems 7 and 9. The CD spectra of the chiral azepine 6 and the chiral phosphoramides 7 and 9 were measured and showed a strong positive CD couplet near 225 nm, consistent with the P axial chirality (S configuration). Semi‐empirical CNDO/S molecular orbital calculations of the CD spectrum of 6 satisfactorily reproduced the major features of the observed spectrum. Chirality 9:431–434, 1997. © 1997 Wiley‐Liss, Inc.