Ti(Oi-Pr)4-Promoted Regio- and Stereoselective Aminolysis of 2,3-Epoxy Amides

被引：2
作者：
Righi, Giuliana [1 ]
Mantineo, Agnese
Suber, Lorenza [2 ]
Mari, Alessandra
机构：
[1] Univ Roma La Sapienza, CNR Ist Chim Biomol, Dip Chim, I-00185 Rome, Italy
[2] CNR Ist Struttura Mat, I-00015 Rome, Italy
来源：
SYNLETT | 2012年 / 13期
关键词：
amides; diastereoselectivity; epoxides; regioselectivity; ring opening; ALPHA; BETA-AZIRIDINE ALDEHYDES; NUCLEOPHILIC OPENINGS; ASYMMETRIC-SYNTHESIS; 1,2-AMINO ALCOHOLS; ANALOGS; EPOXIDES; 1,2-EPOXIDES; DERIVATIVES; AMINES; AGENTS;
D O I：
10.1055/s-0032-1316705
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and inexpensive Ti(Oi-Pr)(4)-mediated aminolysis of 2,3-epoxy amides has been developed. The reaction proceeds with excellent regioselectivity, regardless of the steric hindrance of the substituents on the heterocyclic ring, providing vicinal amino alcohols that are very suitable for synthetic applications.
引用
收藏
页码：1947 / 1949
页数：3
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共 31 条
  • [1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    [J]. CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
  • [2] Long-chain formoterol analogues:: an investigation into the effect of increasing amino-substituent chain length on the β2-adrenoceptor activity
    Alikhani, V
    Beer, D
    Bentley, D
    Bruce, I
    Cuenoud, BM
    Fairhurst, RA
    Gedeck, P
    Haberthuer, S
    Hayden, C
    Janus, D
    Jordan, L
    Lewis, C
    Smithies, K
    Wissler, E
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (18) : 4705 - 4710
  • [3] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .10. SYNTHESIS AND RING-OPENING REACTIONS OF MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS ALIPHATIC OXIRANE SYSTEMS
    AZZENA, F
    CALVANI, F
    CROTTI, P
    GARDELLI, C
    MACCHIA, F
    PINESCHI, M
    [J]. TETRAHEDRON, 1995, 51 (38) : 10601 - 10626
  • [4] The synthesis of vicinal amino alcohols
    Bergmeier, SC
    [J]. TETRAHEDRON, 2000, 56 (17) : 2561 - 2576
  • [5] An efficient asymmetric synthesis of (S)-atenolol:: using hydrolytic kinetic resolution
    Bose, DS
    Narsaiah, AV
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (03) : 627 - 630
  • [6] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING
    CARON, M
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1557 - 1560
  • [7] Scope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines
    Chakraborti, AK
    Kondaskar, A
    Rudrawar, S
    [J]. TETRAHEDRON, 2004, 60 (41) : 9085 - 9091
  • [8] Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening
    Chimni, Swapandeep Singh
    Bala, Neeraj
    Dixit, Vaibhav A.
    Bharatam, Prasad V.
    [J]. TETRAHEDRON, 2010, 66 (16) : 3042 - 3049
  • [9] LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES
    CHINI, M
    CROTTI, P
    FAVERO, L
    MACCHIA, F
    PINESCHI, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (03) : 433 - 436
  • [10] NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ACIDS AND AMIDES MEDIATED BY TI(O-I-PR)4 - RELIABLE C-3 SELECTIVITY
    CHONG, JM
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1560 - 1563
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