Asymmetric alkylation of N-pivaloyl-o-benzylaniline

Wilkinson, James A.; Rossington, Steven B.; Ducki, Sylvie; Leonard, John; Hussain, Nigel

doi:10.1016/j.tetasy.2004.08.020

Cited by 23 publications

(16 citation statements)

References 11 publications

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“…13 C NMR (100 MHz, CDCl 3 ): d = 46.92, 51.08, 54.70, 59.70, 62.64, 67.19, 72.31, 126.3, 127.0, 128.6, 140 ,8.31;N,12.83. Found: C,70.87;H,8.27;N,12.78. (+)-(1R,2S,5S)-3,7-Dimethyl-2-phenyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane (10e) K 2 CO 3 (778 mg, 5.63 mmol) and MeI (351 mL, 799 mg, 5.63 mmol) were added to a solution of 10d (878 mg, 4.02 mmol) in CH 2 Cl 2 (12 mL). After 3 h at r.t., H 2 O (50 mL) was added and the mixture was extracted with CH 2 Cl 2 (4 × 30 mL).…”

Section: (+)-(1r2s5s)-37-dibenzyl-2-phenyl-9-oxa-37-diazabicyclo[mentioning

confidence: 97%

“…7.34;N,7.29. Found: C,81.37;H,7.28;N,7.02. (1R,2S,5S)-3-Benzyl-7-methyl-2-phenyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane (10b) A solution of aqueous methylamine (40%, 48 mL, 556 mmol) and 9 (3.44 g, 7.34 mmol) was stirred for 36 h at 50°C.…”

Section: (+)-(1r2s5s)-37-dibenzyl-2-phenyl-9-oxa-37-diazabicyclo[mentioning

confidence: 98%

“…1 H NMR (400 MHz, CDCl 3 ): d = 2.01 (dd, 1 H, J = 11.9, 3.8 Hz, NCHH), 2.08 (s, 3 H, NCH 3 ), 2.20 (s, 3 H, NCH 3 ), 2.45 (ddd, 1 H, J = 11.4, 3.9, 1.6 Hz, NCHH), 2.70 (ddd, 1 H, J = 11.8, 4.5, 1.7 Hz, NCHH), 2.72 (br d, 1 H, J = 11.8 Hz, NCHH), 3.03 (d, 1 H, J = 11.4 Hz, NCHH), 3.14 (d, 1 H, J = 11.7 Hz, NCHH), 3.46 (d, 1 H, J = 4.0 Hz, NCHPh), 3.67 (br t, 1 H, J = 3.7 Hz, OCH), 3.95 (br t, 1 H, J = 4.1 Hz, OCH), 7.23-7.41 (m, 4 H, ArH), 7.44 (br s, 1 H, ArH). 13 C NMR (100 MHz, CDCl 3 ): d = 42.89, 45.88, 47.32, 53.93, 58.51, 58.95, 68.89, 72.31, 73.19, 127.3, 128.4, 129 ,72.38;H,8.68;N,12.06. Found: C,71.75;H,8.61;N,11.88.…”

Section: (+)-(1r2s5s)-37-dibenzyl-2-phenyl-9-oxa-37-diazabicyclo[mentioning

confidence: 99%

“…Anal. Calcd for C 21 H 27 NO 7 S: C,53.71;H,5.80;N,2.98;S,13.66. Found: C,53.94;H,5.81;N,2.96;S,13.35.…”

mentioning

confidence: 99%

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Enantioselective Synthesis of 2-Phenyl-9-oxabispidines

Breuning¹,

Steiner²

2007

Synthesis

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A small selection of enantiomerically pure 2-phenyl-9-oxabispidines was synthesized in a three to five step procedure from commercially available starting materials. Ring opening of (R,R)-3-phenylglycidol with benzylamine, condensation with (S)-epichlorohydrin to the corresponding cis-2,6-bis(hydroxymethyl)-substituted morpholine intermediate, and final cyclization with a primary amine delivered the desired 2-phenyl-9-oxabispidines in good yields. The substituents at the nitrogen atoms were varied by debenzylation and subsequent alkylation.

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Section: (+)-(1r2s5s)-37-dibenzyl-2-phenyl-9-oxa-37-diazabicyclo[mentioning

confidence: 97%

Section: (+)-(1r2s5s)-37-dibenzyl-2-phenyl-9-oxa-37-diazabicyclo[mentioning

confidence: 98%

Section: (+)-(1r2s5s)-37-dibenzyl-2-phenyl-9-oxa-37-diazabicyclo[mentioning

confidence: 99%

“…Anal. Calcd for C 21 H 27 NO 7 S: C,53.71;H,5.80;N,2.98;S,13.66. Found: C,53.94;H,5.81;N,2.96;S,13.35.…”

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confidence: 99%

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Enantioselective Synthesis of 2-Phenyl-9-oxabispidines

Breuning¹,

Steiner²

2007

Synthesis

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“…Optimization studies are also performed on benzylic protons. ketones [4c,e,j,o,p,q,r,s, 20-28], (iii) the deprotonation of bridgehead carbons followed by either trapping with an electrophile or β-elimination (and thus a ring opening) [4b,g,h,i,k,l,n, [29][30][31][32][33][34], and (iv) the deprotonation of arylic appendages, directly on the aryl moiety or its benzylic position [4f,m, [35][36][37][38][39]. Few other types of transformations have also been explored, which are mentioned at the end of this chapter [40][41][42][43].…”

Section: Chiral Lithium Amides As Basesmentioning

confidence: 99%