(6R)-2-tert-Butyl-6-[(4R,5S)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl]phenol

Abstract

In the title compound, C23H31NO2, the lone pair on the nitro­gen atom is oriented to facilitate intra­molecular hydrogen bonding with the hydr­oxy group residing on the phenyl substituent. The five-membered ring adopts an envelope confornmation with the O atom at the flap. The absolute stereochemistry was verified by measurement of optical activity using a digital polarimeter.

(6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol

“…The title compound is structurally similar to two other oxazolidines published by Koyanagi et al (2010) and Campbell et al (2010). Despite these structural similarities, a Mogul geometry check (Bruno et al, 2004) reveals differences between the three structures.…”

“…We are reporting three related structures containing Jmol enhanced figures, one in this paper and the other two in other papers in this Journal (Campbell et al, 2010;Koyanagi et al, 2010). The Jmol enhanced figures were created to illustrate a range of author convenience versus end user experience, ranging from a purely GUI driven experience for the author resulting in a less functional figure for the end user to a more sophisticated use of the Jmol scripting by the author resulting in a more polished and versatile figure for the end user.…”

“…For related structures and background to the use of chiral oxazolidines as templates in asymmetric synthesis, see: Agami & Couty (2004); Campbell et al (2010); Koyanagi et al (2010); Parrott & Hitchcock (2007); Parrott et al (2008). The synthesis of the title compound is described by Parrott & Hitchcock (2007).…”

(6S)-2,4-Di-tert-butyl-6-[(4S,5R)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl]phenol

“…The procedure for recreating the Jmol figure is provided in the hope that readers will find it useful for creating their own. We are reporting three related structures containing Jmol enhanced figures, one in this paper and the other two in other papers in this Journal (Anderson et al, 2010;Koyanagi et al, 2010). The Jmol enhanced figures were created to illustrate a range of author convenience versus end user experience, ranging from a purely GUI driven experience for the author resulting in a less functional figure for the end user to a more sophisticated use of the Jmol scripting by the author resulting in a more polished and versatile figure for the end user.…”

“…For related structures and background to chiral oxazolidines, see: Agami & Couty (2004); Anderson et al (2010); Bourne et al (1997); Duffy et al (2004); Hitchcock et al (2004); Koyanagi et al (2010); Parrott & Hitchcock (2007); Parrott et al (2008). The synthesis and absolute configuration assignment of the title compound is described by Parrott et al (2008).…”