Copper(I) Chloride Mediated Cyclization of Optically Active 2,3-Allenoic Acids or 1:1 Salts of Optically Active 2,3-Allenoic Acids with Chiral Amines

Abstract

Copper(I) chloride mediated cyclization of optically active 2,3-allenoic acids or 1:1 salts of optically active 2,3-allenoic acids with chiral amines was developed. The reaction of optically active 2,3-allenoic acids in methanol requires only a catalytic amount of copper(I) chloride, while the reaction of the 1:1 salts of optically active 2,3-allenoic acids with chiral amines needs one equivalent of copper(I) chloride and should be carried out in dichloromethane to ensure high efficiency of chirality transfer.

chirality transfer - cyclization - copper(I) chloride - amines - 2,3-allenoic acids

References

<A NAME="RF06706SS-1A">1a</A> Larock RD. Riefling B. Fellows CA. J. Org. Chem.  1978,  43:  131 ; and references cited therein

<A NAME="RF06706SS-1B">1b</A> Brima TS. inventors; US  4968817.  ; Chem. Abstr. 1991, 114, 185246y

<A NAME="RF06706SS-1C">1c</A> Tanabe A. inventors; Jpn. Kokai Tokyo Koho JP 63211276  [88211276].  ; Chem. Abstr. 1989, 110, 94978q

<A NAME="RF06706SS-1D">1d</A> Lee GCM. inventors; Eur. Pat. Appl. EP  372940.  ; Chem. Abstr. 1990, 113, 191137j

<A NAME="RF06706SS-1E">1e</A> Ducharme Y, Gauthier JY, Prasit P, Leblanc Y, Wang Z, Leger S, and Therien M. inventors; PCT Int. Appl. WO 95  00501.  ; Chem. Abstr. 1996, 124, 55954y

<A NAME="RF06706SS-1F">1f</A> Lee Gary CM, and Garst ME. inventors; PCT Int. Appl. WO 91  16055.  ; Chem. Abstr. 1992, 116, 59197m

For some recent examples, see:

<A NAME="RF06706SS-2A">2a</A> Chia Y. Chang F. Wu Y. Tetrahedron Lett.  1999,  40:  7513 

<A NAME="RF06706SS-2B">2b</A> Takahashi S. Maeda K. Hirota S. Nakata T. Org. Lett.  1999,  1:  2025 

<A NAME="RF06706SS-2C">2c</A> Siddiqui BS. Afshan F. . Faizi S. Naqvi SN.-H. Tariq RM. J. Chem. Soc., Perkin Trans. 1  1999,  2367 

<A NAME="RF06706SS-2D">2d</A> Cortez DAG. Fernandes JB. Vieria PC. Silva MFGF. Ferreira AG. Cass QB. Pirani JR. Phytochemistry  1998,  49:  2493 

<A NAME="RF06706SS-2E">2e</A> Otsuka H. Kotani K. Bando M. Kido M. Takeda Y. Chem. Pharm. Bull.  1998,  46:  1180 

<A NAME="RF06706SS-2F">2f</A> Guo S. Wang L. Chen D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1997,  36:  339 

<A NAME="RF06706SS-2G">2g</A> Evidente A. Sparapano L. J. Nat. Prod.  1994,  57:  1720 

<A NAME="RF06706SS-2H">2h</A> Damtoft S. Jensen SR. Phytochemistry  1995,  40:  157 

<A NAME="RF06706SS-2I">2i</A> Estevez-Reyes R. Estevez-Braun A. Gonzalez AG. J. Nat. Prod.  1993,  56:  1177 

<A NAME="RF06706SS-2J">2j</A> Claydon N. Hanson JR. Truneh A. Avent AG. Phytochemistry  1991,  30:  3802 

<A NAME="RF06706SS-2K">2k</A> Seki T. Satake M. Mackenzie L. Kaspar HF. Yasumoto T. Tetrahedron Lett.  1995,  36:  7093 

<A NAME="RF06706SS-2L">2l</A> Marshall JA. Wolf MA. Wallace EM. J. Org. Chem.  1997,  62:  367 

<A NAME="RF06706SS-3A">3a</A> Basabe P. Delgado S. Marcos IS. Diez D. Diego A. De Roman M. Urones JG. J. Org. Chem.  2005,  70:  9480 

<A NAME="RF06706SS-3B">3b</A> Naito S. Escobar M. Kym PR. Liras S. Martin SF. J. Org. Chem.  2002,  67:  4200 

<A NAME="RF06706SS-3C">3c</A> Jiang S. Liu Z.-H. Sheng G. Zeng B.-B. Cheng X.-G. Wu Y.-L. Yao Z.-J. J. Org. Chem.  2002,  67:  3404 

<A NAME="RF06706SS-3D">3d</A> Busqué F. March P. Figueredo M. Font J. Sanfeliu E. Tetrahedron Lett.  2002,  43:  5583 

<A NAME="RF06706SS-3E">3e</A> Yoneda E. Kaneko T. Zhang S. Onitsuka K. Takahashi S. Org. Lett.  2000,  2:  441 

<A NAME="RF06706SS-3F">3f</A> Brown SP. Goodwin NC. MacMillan DWC. J. Am. Chem. Soc.  2003,  125:  1192 

<A NAME="RF06706SS-4A">4a</A> Ma S. Shi Z. Yu Z. Tetrahedron Lett.  1999,  40:  2393 

<A NAME="RF06706SS-4B">4b</A> Ma S. Shi Z. Yu Z. Tetrahedron  1999,  40:  12137 

<A NAME="RF06706SS-4C">4c</A> Fu C. Ma S. Eur. J. Org. Chem.  2005,  3942 

<A NAME="RF06706SS-4D">4d</A> Ma S. Yu Z. Angew. Chem. Int. Ed.  2002,  41:  1775 

<A NAME="RF06706SS-4E">4e</A> Ma S. Yu Z. Chem. Eur. J.  2004,  10:  2078 

<A NAME="RF06706SS-4F">4f</A> Ma S. Yu Z. Org. Lett.  2003,  5:  1507 ; corrigendum Org. Lett. 2003, 5, 2581

<A NAME="RF06706SS-4G">4g</A> Ma S. Yu Z. J. Org. Chem.  2003,  68:  6149 

<A NAME="RF06706SS-4H">4h</A> Ma S. Gu Z. J. Am. Chem. Soc.  2005,  127:  6182 

<A NAME="RF06706SS-4I">4i</A> Ma S. Yu Z. Gu Z. Chem. Eur. J.  2005,  11:  2351 

<A NAME="RF06706SS-5">5</A> For copper(I) chloride catalyzed cycloisomerization of racemic 2,3-allenoic acids, see: Ma S. Yu Z. Wu S. Tetrahedron  2001,  57:  1585 

<A NAME="RF06706SS-6A">6a</A> Ma S. Shi Z. Chem. Commun.  2002,  540 

<A NAME="RF06706SS-6B">6b</A> Ma S. Wu S. Chem. Commun.  2001,  441 

<A NAME="RF06706SS-7">7</A>

Crystal data for compound (R)-(+)-2e: C₁₃H₁₃BrO₂, M = 281.14, monoclinic, space group P2 (1), Mo Kα, final R indices [I > 2σ(I)], R1 = 0.0657, wR2 = 0.1570, a = 4.3321 (19) Å, b = 10.916 (5) Å, c = 13.117 (6) Å, α = 90°, β = 92.942 (7)°, γ = 90°, V = 619.5 (5) ų, T = 293 (2) K, Z = 2, reflections collected/unique: 3518:2213 (R _int = 0.1593), no observation [I > 2σ(I)] 957, parameters 155; CCDC 602980 contains the data.

<A NAME="RF06706SS-8A">8a</A> Ma S. Yu Z. J. Org. Chem.  2003,  68:  6149 

<A NAME="RF06706SS-8B">8b</A> Ma S. Yu Z. Angew. Chem. Int. Ed.  2003,  42:  1955 

<A NAME="RF06706SS-8C">8c</A> Ma S. Yu Z. Gu Z. Chem. Eur. J.  2005,  11:  2351