References and Notes
1
List B.
Lerner RA.
Barbas III CF.
J.
Am. Chem. Soc.
2000,
122:
2395
2a
Dalko PI.
Moisan L.
Angew.
Chem. Int. Ed.
2001,
40:
3726
2b
Dalko PI.
Moisan L.
Angew. Chem.
Int. Ed.
2004,
43:
5138
2c
Xiong Y.
Wen YH.
Wang F.
Gao B.
Liu XH.
Huang X.
Feng XM.
Adv.
Synth. Catal.
2007,
349:
2156
2d
Yang ZG.
Liu J.
Liu XH.
Wang Z.
Feng XM.
Su ZS.
Hu CW.
Adv. Synth. Catal.
2008,
350:
2001
2e
Liu J.
Yang ZG.
Wang Z.
Wang F.
Chen XH.
Liu XH.
Feng XM.
Su ZS.
Hu
CW.
J. Am. Chem. Soc.
2008,
130:
5654
2f
Wang F.
Xiong Y.
Liu XH.
Feng XM.
Adv. Synth. Catal.
2007,
349:
2665
2g
Chen XH.
Wang J.
Zhu Y.
Shang DJ.
Gao B.
Liu XH.
Feng XM.
Su ZS.
Hu CW.
Chem. Eur.
J.
2008,
14:
10896
3a
Marigo M.
Fielenbach D.
Braunton A.
Kjærsgaard A.
Jørgensen KA.
Angew.
Chem. Int. Ed.
2005,
44:
3703
3b
Marigo M.
Wabnitz TC.
Fielenbach D.
Jørgensen KA.
Angew.
Chem. Int. Ed.
2005,
44:
794
4a
Ouellet SG.
Tuttle JB.
MacMillan DWC.
J.
Am. Chem. Soc.
2005,
127:
32
4b
Northrup AB.
Mangion
IK.
Hettche F.
MacMillan DWC.
Angew. Chem. Int. Ed.
2004,
43:
2152
5a
Torii H.
Nakadai M.
Ishihara K.
Saito S.
Yamamoto H.
Angew. Chem. Int. Ed.
2004,
43:
1983
5b
Saito S.
Yamamoto H.
Acc. Chem. Res.
2004,
37:
570
6a
Tang Z.
Jiang F.
Yu L.-T.
Cui X.
Gong L.-Z.
Mi A.-Q.
Jiang Y.-Z.
Wu Y.-D.
J. Am. Chem. Soc.
2003,
125:
5262
6b
Tang Z.
Jiang F.
Cui X.
Gong L.-Z.
Mi
A.-Q.
Jiang Y.-Z.
Wu Y.-D.
Proc. Natl.
Acad. Sci. U.S.A.
2004,
101:
5755
7
Chen J.-R.
Lu H.-H.
Li X.-Y.
Cheng L.
Wan J.
Xiao W.-J.
Org.
Lett.
2005,
7:
4543
8
Wu Y.-Y.
Zhang Y.-Z.
Yu M.-L.
Zhao G.
Wang S.-W.
Org.
Lett.
2006,
8:
4417
9
Dinér P.
Amedjkouh M.
Org. Biomol. Chem.
2006,
4:
2091
10
Liu X.-W.
Le TN.
Lu Y.-P.
Xiao Y.-J.
Ma J.-M.
Li X.-W.
Org. Biomol. Chem.
2008,
6:
3997
11
Xin J.-G.
Chang L.
Hou Z.-R.
Shang D.-J.
Liu X.-H.
Feng X.-M.
Chem. Eur. J.
2008,
14:
3177
12 Analytical data for compound 1: yield 78%; mp 182-186 ˚C. ¹H
NMR (300 MHz, DMSO-d
6): δ = 10.23
(s, 3 H, CONH), 8.02-8.06 (d, 3 H, J = 13.1
Hz, ArH), 7.89-7.92 (d, 3 H, J = 7.9
Hz, ArH), 7.45-7.48 (m, 3 H, ArH), 7.20-7.26 (m,
3
H, ArH), 3.69-3.74 (m, 3 H, CH), 3.46 (m, 3 H, NH), 2.89 (m,
6 H, CH2), 1.47-2.03 (m, 12 H, CH2). ¹³C
NMR (75 MHz, DMSO-d
6): δ = 26.09,
30.79, 47.10, 61.17, 122.30, 122.45, 123.09, 126.65, 126.77, 129.57,
129.74, 132.99, 134.35, 139.30, 139.49, 173.73. ³¹P
NMR (202 MHz, DMSO-d
6): δ = 26.85
(s). IR (KBr disc): 1687 (CONH)
cm-¹.
ESI-MS: m/z = 637.42 [M + Na+].
Anal. Calcd (%) for C33H39N6O4P:
C, 64.48; H, 6.39; N, 13.67. Found: C, 64.46; H, 6.40; N, 13.66.
13 Analytical data for compound 2: yield 99%; mp 212-218 ˚C. ¹H
NMR (300 MHz, DMSO-d
6): δ = 10.17
(s, 3 H, CONH), 8.02-8.06 (d, 3 H, J = 13.1
Hz, ArH), 7.88-7.91 (d, 3 H, J = 8.0
Hz, ArH), 7.43-7.49 (m, 3 H, ArH), 7.19-7.25 (m,
3
H, ArH), 4.74 (br, 3 H, OH), 4.19 (s, 3 H, CH), 3.82-3.87 (t,
3 H, J = 8.2
Hz, CHOH), 3.42 (m, 3 H, NH), 2.73-2.88 (m, 6 H, CH2),
1.75-1.96 (m, 6 H, CH2). ¹³C
NMR (75 MHz, DMSO-d
6): δ = 49.02,
55.56, 60.41, 71.86, 79.74, 122.34, 122.49, 123.12, 126.59, 126.72,
129.50, 129.68, 132.94, 134.30, 139.32, 139.51, 174.27. ³¹P
NMR (202 MHz, DMSO-d
6): δ = 27.13
(s). IR (KBr disc): 1680 (OC=O, CONH) cm-¹.
ESI-MS: m/z = 685.33 [M + Na+].
Anal. Calcd (%) for C33H39N6O7P:
C, 59.81; H, 5.93; N, 12.68. Found: C, 59.78; H, 5.96; N, 12.66.
14 Analytical data for compound 3: yield 92%; mp 212-218 ˚C. ¹H
NMR (300 MHz, DMSO-d
6): δ = 9.78
(s, 3 H, NH), 7.48 (s, 3 H, ArH), 7.27 (m, 3 H, ArH), 3.64-3.67
(m, 3 H, CH), 3.60-3.62 (m, 6 H, CH2), 3.06-3.10
(d, 6 H, J = 13.1
Hz, PCH2), 2.87 (t, 6 H, J = 6.4
Hz, CH2), 2.19 (s, 9 H, ArCH3), 1.69-2.07
(m, 6 H, CH2), 1.49-1.67 (m, 12 H, CH2),
1.27-1.39 (m, 27 H, CH2), 0.88 (t, 9 H, J = 7.3 Hz,
CH3). ¹³C NMR (75 MHz, DMSO-d
6): δ = 14.20,
16.85, 19.20, 28.38, 28.42, 28.66, 28.76, 32.22, 55.34, 59.84, 68.40,
69.03, 72.74, 78.94, 79.05, 120.37, 121.00, 126.04, 131.18, 134.98, 135.07,
151.81, 153.80, 154.22, 171.08, 171.48. ³¹P
NMR (202 MHz, DMSO-d
6): δ = 42.23
(s). ESI-MS: m/z = 937.75 [M + Na+].
Anal. Calcd (%) for C51H75N6O7P:
C, 66.94; H, 8.26; N, 9.18. Found: C, 66.93; H, 8.29; N, 9.17.
15 Analytical data for compound 4: yield 65%; mp 212-218 ˚C. ¹H
NMR (300 MHz, DMSO-d
6): δ = 9.77
(s, 3 H, NH), 7.46 (s, 3 H, ArH), 7.25 (s, 3 H, ArH), 4.77 (s, 3
H, OH), 4.17 (s, 3 H, CH), 3.80 (t, 3 H, J = 8.1
Hz, CH), 3.60 (t, 6 H, J = 6.3 Hz,
CH2), 3.03-3.07 (d, 6 H, J = 13.2
Hz, PCH2), 2.74-2.88 (m, 6 H, CH2),
2.17 (s, 9 H, ArCH3), 1.67-2.00 (m, 6 H, CH2),
1.47-1.56 (m, 6 H, CH2), 1.27-1.35
(m, 6 H, CH2), 0.87 (t, 9 H, J = 7.2
Hz,CH3). ¹³C NMR (75 MHz,
DMSO-d
6): δ = 14.29,
16.76, 19.22, 29.45, 30.24, 32.25, 55.53, 60.34, 71.89, 72.81, 120.17,
120.97, 126.09, 126.19, 131.25, 134.30, 151.75, 151.82, 173.28. ³¹P
NMR (202 MHz, DMSO-d
6): δ = 42.56
(s). ESI-MS: m/z = 985.67 [M + Na+]. Anal.
Calcd (%) for C51H75N6O10P:
C, 63.60; H, 7.85; N, 8.73. Found: C, 63.61; H, 7.88; N, 8.75.
16
Zheng J.-F.
Li Y.-X.
Zhang S.-Q.
Yang S.-T.
Wang X.-M.
Wang Y.-Z.
Bai J.
Liu F.-A.
Tetrahedron Lett.
2006,
47:
7793
17 Compound 5a:
reaction time: 72 h; yield: 89%;
anti/syn = 85:15;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 95:5,
flow rate: 1.0 mL/min, 25 ˚C, UV: λ =
254
nm): t
R(minor) = 43.6
min, tR(major) = 59.2 min.
Compound 5b: reaction time: 72 h; yield: 88%;
anti/syn = 82:18;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 95:5,
flow rate: 1.0 mL/min, 20 ˚C, UV: λ =
254
nm): t
R(major) = 37.8
min, t
R(minor) = 46.5
min.
Compound 5c: reaction time:
72 h; yield: 78%;
anti/syn = 88:12;
HPLC (Chiralcel OD-H, hexane-i-PrOH = 95:5,
flow rate: 1.0 mL/min, 20 ˚C, UV: λ =
254
nm ): t
R(major) = 13.8
min, tR(minor) = 16.0 min.
Compound 5d: reaction time: 120 h; yield: 81%;
anti/syn = 79:21;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 90:10,
flow rate: 0.5 mL/min, 17 ˚C, UV: λ =
254
nm): tR(major) = 26.5 min,
tR(minor) = 20.7 min.
Compound 5e: reaction time: 120 h; yield: 81%;
anti/syn = 80:20;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 90:10,
flow rate: 0.5 mL/min, 21 ˚C, UV: λ = 220nm): t
R(major) = 27.7
min, tR(minor) = 31.2 min.
Compound 5f: reaction time: 120 h; yield: 87%;
anti/syn = 67:33;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 90:10,
flow rate: 0.5 mL/min, 17 ˚C, UV: λ =
254
nm): tR(minor) = 40.1 min,
tR(major) = 60.7 min.
Compound 5g: reaction time: 120 h; yield: 92%;
anti/syn = 85:15;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 95:5,
flow rate: 0.5 mL/min, 21 ˚C, UV: λ =
220
nm): t
R(major) = 31.1
min, t
R(minor) = 36.9
min.
Compound 5h: reaction time:
120 h; yield: 68%;
anti/syn = 78:22;
HPLC (Chiralcel OD-H, hexane-i-PrOH = 90:10,
flow rate: 1.0 mL/min, 20 ˚C, UV: λ =
220
nm): t
R(major) = 9.6
min, t
R(minor) = 14.3
min.
Compound 5i: reaction time:
120 h; yield: 43%;
anti/syn = 83:17;
HPLC (Chiralcel AD-H, hexane-i-PrOH = 90:10,
flow rate: 1.0 mL/min, 21 ˚C, UV: λ =
254
nm): t
R(major) = 18.5
min, t
R(minor) = 10.2
min.
18
Xiong Y.
Wang F.
Dong S.-X.
Liu X.-H.
Feng X.-M.
Synlett
2008,
73