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Synthesis 2003(9): 1441-1445
DOI: 10.1055/s-2003-40189
DOI: 10.1055/s-2003-40189
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New YorkDiastereoselective 1,3-Dipolar Cycloaddition of Ynolates with Chiral Nitrones
Further Information
Received
28 April 2003
Publication Date:
24 June 2003 (online)
Publication History
Publication Date:
24 June 2003 (online)

Abstract
Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with chiral nitrones produced 5-isoxazolidinones with good diastereoselectivity. These products were easily converted into optically pure β-amino acids and chiral γ-butyrolactones.
Key words
asymmetric synthesis - cycloadditions - diastereoselectivity - nitrones - ynolates
- 1
Shindo M.Itoh K.Tsuchiya C.Shishido K. Org. Lett. 2002, 4: 3119 - For a recent review on β-amino acids and β-peptides see:
- 2a
Cheng RP.Gellman SH.DeGrado WF. Chem. Rev. 2001, 101: 3219 - 2b
Abele S.Seebach D. Eur. J. Org. Chem. 2000, 1 - 2c
Cardillo G.Tomasini C. Chem. Soc. Rev. 1996, 117 - For reviews see:
- 3a
Shindo M. Chem. Soc. Rev. 1998, 27: 367 - 3b
Shindo M. J. Synth. Org. Chem. Jpn. 2000, 58: 1155 - 3c
Shindo M. Yakugaku Zasshi 2000, 120: 1233 - 4a
Shindo M. Tetrahedron Lett. 1997, 38: 4433 - 4b
Shindo M.Sato Y.Shishido K. Tetrahedron 1998, 54: 2411 - 4c
Shindo M.Koretsune R.Yokota W.Itoh K.Shishido K. Tetrahedron Lett. 2001, 42: 8357 - 4d
Shindo M.Sato Y.Shishido K. J. Am. Chem. Soc. 1999, 121: 6507 - 4e
Shindo M.Sato Y.Shishido K. J. Org. Chem. 2001, 66: 7818 - 4f
Shindo M.Sato Y.Shishido K. Tetrahedron Lett. 2002, 43: 5039 - 4g
Shindo M.Matsumoto K.Sato Y.Shishido K. Org. Lett. 2001, 3: 2029 - 4h
Shindo M.Oya S.Murakami R.Sato Y.Shishido K. Tetrahedron Lett. 2000, 41: 5943 - 4i
Shindo M.Sato Y.Shishido K. Tetrahedron Lett. 1998, 39: 4857 - 4j
Shindo M.Sato Y.Shishido K. J. Org. Chem. 2000, 65: 5443 - 4k
Shindo M.Matsumoto K.Mori S.Shishido K. J. Am. Chem. Soc. 2002, 124: 6840 - 5a
Merino P.Franco S.Merchan FL.Tejero T. Tetrahedron: Asymmetry 1997, 8: 3489 - 5b
Merino P.Castillo E.Franco S.Merchan FL.Tejero T. Tetrahedron: Asymmetry 1998, 9: 1759 - 6 For a review see:
Merino P.Franco S.Merchan FL.Tejero T. Synlett 2000, 442 - 7
Moglioni AG.Muray E.Castillo JA.Alvarez-Larena A.Moltrasio GY.Branchadell V.Ortuno RM. J. Org. Chem. 2002, 67: 2402 - 8 Addition of the enolate of methyl
acetate was reported: see
Merino P.Franco S.Garces N.Merchan FL.Tejero T. Chem. Commun. 1998, 493 - 9
Shindo M.Sato Y.Koretsune R.Yoshikawa T.Matsumoto K.Shishido K. Chem. Pharm. Bull. 2003, 51: 477