A concise enantioselective synthesis of allylamines and N-boc-β-amino acids (original) (raw)

1994, Tetrahedron Letters

Abstmctz A new and efficient enanksektiie synthesis of allylamines and KBoc-B_amho acids has been developed. Statting from enaniiomerically enriched Mdiphenylmethyl-3_aminol,2dii. allylamines are easily obtained by a Corey-Hopkins deoxyganative protocol. After a change in the nitrogen protecting gruup, the resulting KBoc allylamines are converted into ~-amino acids by hydroboration with 9-BEN falbwed by oxidation with PDC in DMF. scalemic N-diphenylmethyl-3-amino-1,2-diols (1) as starting materials for the enantioselective preparation of az?tidinols,lo aziridineslc and a-am ino acids -11 ,I* We describe in the present communication the successful conversion of 1 into allylamines and, subsequently, into p-amino acids. R; $ 0" -R 'I' COO" PhYN-" PGdN'H PGeN'H Ph 1 § Dedicated to Professor Pedro Victory on the ocassion of his 65th birthday. A., Tetrahao?un Leti. 1991, 32,693l G Poch. M.; Vetdaguer. X.; Moyano, A.; Peri&% MA.; Riera, A., Tetrahedron Lett. 1221. 32.8935. Poch, M.; Alcc)n, M.; Moyano, A.; Petis. M.A.: Riera, A., Tetmkhn L&t. 1993, 34. 0666. 12: Cast-, P.; Moyano.A.; Perk&s, MA; Ri,A. SyndhebCofnftnut., inpress. 13.-(a) Linz, Z.; Classon. B. J. Org. C&m. loQo.55, 4273. (b)Crank, G.; Eastwood. F.W. Ausfm!. J. Chem. 1264, 17, 1392. (c) Hanaasian, S.; Sargiotti, A.; LaRue, M. Tetmhedtvn Letf. 1976. 737. (d) Corey, E.J.; Winter, R.A.E. J. Am. Chem. Soo. lQ83,85,2677. 14.-Corey, E.J.; Hop&ins, P.B. Tefmhedrun Lett.1982.23, 1979. 15.-For the diiereosakct ive hydmboration of Nbenzyl-Ntoql a-subetkuted altylamines. see ref. 6e. 16.-Barton, D.H.R.; Subramanian, R. J. Chsm. Sot., P&in Trans. 11977, 1718. 17.-These compounds have been prepared in very high yield from Ihe correqomEng Ndiphenylmelhyl-3-amino-1,2diils by a one-pal procedure (HdPd(OH)2 cat.IBoqCMeOH). See ref. il. 16.-Corey, EJ.; Schmidt, G. Tetrahedron Leti. 1979,399. 19.-Casara, P.; Danzin, C.; Metcalf, 8.; Jung, M. J. Chsm. Sot., Perkin Trans. 11963,2201. 2O.-McIntosh, J.M.; Acquaah. S.O. Can. J. Chem. lW3.56, 1752. 21.-For recent enantioselective syntheses of allylamines see: (a) Grossman, R.B.; Davis, W-M.; Btichwald, S.L. J. Am. Chem. Sot. 1991, 113,232l. (b) Whilesell, J.K.; Yaser, H.K. J. Am. Chem. Sot. 1931, I19 3526. (c) Enders. 0.;