The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2733-2735

  Liu, Da Xue ^a   Zhang, Li Cheng ^a   Wang, Quan ^a   Da, Chao Shan ^a   Xin, Zhuo Qun ^a   Wang, Rui ^a   Choi, Michael C K ^b   Chan, Albert S C ^b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013035824     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016341e     Document Type: Article

References (32)

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29. 3) δ 0.74 (d, 3H, J = 5 Hz), 0.98 (d, 3H, J = 6.7 Hz), 1.49 (d, 3H, J = 6.7 Hz), 2.18 (senary, 1H, J = 6.7 Hz), 3.00 (t, 1H, J = 6.7 Hz), 2.50 (br s, 1H), 4.15 (d, 1H, J = 6 Hz), 7.05-7.70 (m, 11H), 13.01 (br s, 1H); MS (M + 1)320.16.
30. 3) δ 1.57 (d, 3H, J = 6.6 Hz), 2.14 (s, 3H), 3.75 (q, 1H, J = 6.6 Hz), 5.35 (s, 1H), 7.21-7.81 (m, 16H), 13.82 (br s, 1H); MS (M + 1) 368.16.
31. 2Zn (2.84 mL, 1 M in hexane) at room temperature. After the mixture stirred for 1 h, benzaldehyde (100 mg, 0.947 mmol) was added at room temperature, and the reaction was stirred for 24 h at room temperature. Optically active 1-phenylpropan-1-o1 (124 mg, 97%) was obtained after acid workup and purification by silica gel TLC.
32. 2 = 0.1190, SADABS (semiempirical).